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Triethylamine → HCID 118157989, compound

HRID 1779203
Notes
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Reaction equation

HRID 1779203 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:60])([F:59])[F:58])=O.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[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])([CH2:52][CH2:53][O:55][C:56](=[O:61])[C:57]([F:60])([F:59])[F:58])[C:23]([OH:25])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

HCID 118157989HCID 118157989, compound

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 (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 by LCMS, formic acid (5.0 mL) was added and the mixture was stirred overnight. The solvent was distilled off under reduced pressure to obtain (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-12-oxo-2-[2-(2,2,2-trifluoro-acetoxy)-ethyl]-nonadec-4-enoic acid (ESI (LC/MS positive mode) m/z 740 (M+H); Rt 2.64 min.). To the obtained (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-hydroxy-12-oxo-2-[2-(2,2,2-trifluoro-acetoxy)-ethyl]-nonadec-4-enoic acid (16 mg, 0.0216 mmol) were added toluene (3.0 mL), methanol (1.0 mL), and trimethylsilyldiazomethane (0.6 M in n-hexane, 54 μL, 0.0324 mmol), and the mixture was stirred at room temperature. After being stirred for 1.5 hours, trimethylsilyldiazomethane (0.6 M in n-hexane, 54 μL, 0.0324 mmol) was added. After stirring for 1 hour, the organic solvent was distilled off under reduced pressure. The resulting residue was purified by preparative HPLC and then freeze-dried to obtain the title compound (17 mg, 99% yield, white solid).

Workup

  1. additionTo a mixture of No
  2. stirringAfter being stirred for 3 hours
  3. customthe consumption of No
  4. addition5217614 by LCMS, formic acid (5.0 mL) was added
  5. stirringthe mixture was stirred overnight
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1c119c86cab64ab0b48588dc4316a3e0
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266853B2

Reaction notes

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