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Triethylamine → HCID 90060133, compound

HRID 1779201
Notes
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Reaction equation

HRID 1779201 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C@@:22]([OH:33])(CCO)[C:23]([O:25]C(C)(C)C)=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].F[C:52](F)(F)[C:53]([O:55][C:56](=[O:61])[C:57](F)(F)F)=O.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[C:56]([O:55][CH2:53][CH2:52][C@:22]([OH:33])([C@@H:21]([C:19](=[O:20])[NH:18][C@H:13]([C:14]([O:16][CH3:17])=[O:15])[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:11][CH:10]=1)/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42](=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[C:23]([OH:25])=[O:24])(=[O:61])[CH3:57]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydride2×HCID 90060183HCID 90060183, compound

Product 1

HCID 90060133HCID 90060133, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

To a mixture of No. 5217614, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate (150 mg, 0.214 mmol) and dichloromethane (15 mL) were added trifluoroacetic acid anhydride (TFAA, 36 μL, 0.258 mmol), triethylamine (89 μL, 0.642 mmol), and DMAP (1.3 mg, 0.0107 mmol), and the mixture was stirred at room temperature. After being stirred for 3 hours, trifluoroacetic acid anhydride (72 μL, 0.516 mmol) was added again. After confirming the consumption of No. 5217614 tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate by LCMS, formic acid (5 mL) was added and the mixture was stirred overnight. The solvent was distilled off under reduced pressure. THF (5 mL) and a saturated aqueous solution (0.5 mL) of NaHCO3 were then added and the mixture was stirred at room temperature for 10 minutes. The solvent was distilled off under reduced pressure. The residue was then purified by preparative HPLC. The purified fraction was freeze-dried to obtain the title compound (67 mg, 48% yield, yellow oil).

Workup

  1. additionTo a mixture of No
  2. stirringAfter being stirred for 3 hours
  3. customthe consumption of No
  4. addition5217614 tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate by LCMS, formic acid (5 mL) was added
  5. stirringthe mixture was stirred overnight
  6. distillationThe solvent was distilled off under reduced pressure
  7. additionTHF (5 mL) and a saturated aqueous solution (0.5 mL) of NaHCO3 were then added
  8. stirringthe mixture was stirred at room temperature for 10 minutes
  9. distillationThe solvent was distilled off under reduced pressure
  10. customThe residue was then purified by preparative HPLC
  11. customThe purified fraction was freeze-dried

Sources & evidence

ORD record
ord-e228825b333b476c83479e5345df7a41
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266853B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes