Acetic Anhydride → HCID 90060205, compound

HRID 1779200Notes

Reaction equation

HRID 1779200 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])([CH2:30][CH2:31][OH:32])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[C:51](OC(=O)C)(=[O:53])[CH3:52].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl>[C:51]([O:32][CH2:31][CH2:30][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]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])(=[O:53])[CH3:52]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 90060183HCID 90060183, compound

Product 1

HCID 90060205HCID 90060205, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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, Compound D (13.7 g, 19.6 mmol) was dissolved in dichloromethane (274 mL), and then acetic anhydride (4.64 mL, 49.1=mop, triethylamine (2.74 mL, 19.7 mmol), and dimethylaminopyridine (240 mg, 1.96 mmol) were added at 0° C. After stirring for 1.5 hours, the mixture was quenched with water (195 mL) and then separated. The aqueous layer was extracted with dichloromethane (195 mL). The dichloromethane layers were combined, then washed with a saturated aqueous solution (140 mL) of sodium chloride, then dried over anhydrous sodium sulfate, and filtered. The organic layer was concentrated under reduced pressure. The residue was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 11.0 g (14.8 mmol, yield 76%) of No. 5318799 (Compound R).

Workup

  1. customthe mixture was quenched with water (195 mL)
  2. customseparated
  3. extractionThe aqueous layer was extracted with dichloromethane (195 mL)
  4. washwashed with a saturated aqueous solution (140 mL) of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customThe residue was purified on Biotage (silica gel, n-hexane/ethyl acetate)
  9. customto obtain 11.0 g (14.8 mmol, yield 76%) of No

Sources & evidence

ORD record
ord-e18070f920ba4e61aa7a08501b1d38e3
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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