Acetic Anhydride → HCID 118260144, compound

HRID 1779204Notes

Reaction equation

HRID 1779204 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([NH:21][C:22]([C@@H:24](/[CH:37]=[CH:38]/[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45](=[O:53])[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C@@:25]([OH:36])([CH2:33][CH2:34][OH:35])[C:26]([O:28][C:29](C)(C)C)=[O:27])=[O:23])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]#[C:19][CH3:20])=[CH:12][CH:11]=1)=[O:7])(C)(C)C.C(OC(=O)C)(=O)C.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH2:17]([O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C@H:8]([NH:21][C:22]([C@@H:24](/[CH:37]=[CH:38]/[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45](=[O:53])[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[C@@:25]([OH:36])([CH2:33][CH2:34][OH:35])[C:26]([O:28][CH3:29])=[O:27])=[O:23])[C:6]([O:5][CH3:1])=[O:7])=[CH:15][CH:14]=1)[C:18]#[C:19][CH3:20]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 90060200HCID 90060200, compound

Product 1

HCID 118260144HCID 118260144, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of No. 4984967, tert-butyl (E)-(2S,3S)-3-[(S)-1-tert-butoxycarbonyl-2-(4-but-2-ynyloxy-phenyl)-ethylcarbamoyl]-2-hydroxy-2-(2-hydroxy-ethyl)-12-oxo-nonadec-4-enoate (112 mg, 0.152 mmol) and dichloromethane (1.3 mL) was cooled to 4° C., and acetic anhydride (35.8 μL, 0.379 mmol), triethylamine (23.3 μL, 0.167 mmol), and DMAP (1.9 mg, 0.02 mmol) were added. After stirring for 2 hours, the consumption of the starting materials was confirmed by LCMS. The solvent was distilled off under reduced pressure. Formic acid (10 mL) was added and the mixture was stirred at room temperature for 15 hours. Formic acid was distilled off under reduced pressure. The resulting residue was purified by preparative HPLC and then freeze-dried to obtain the title compound (46 mg, 45% yield, colorless oil).

Workup

  1. additionA mixture of No
  2. customthe consumption of the starting materials
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionFormic acid (10 mL) was added
  5. stirringthe mixture was stirred at room temperature for 15 hours
  6. distillationFormic acid was distilled off under reduced pressure
  7. customThe resulting residue was purified by preparative HPLC
  8. customfreeze-dried

Sources & evidence

ORD record
ord-ae424ffa72ca4a03bef8d134d5906879
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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