Acetyl chloride → (2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methyl-cyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester

HRID 20427Notes

Reaction equation

HRID 20427 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([O:9][C:10]([N:12]1[C@@H:17]([CH:18]([OH:36])[CH:19]([NH2:35])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:22]=2)[CH2:16][O:15][C@@H:14]([O:37][CH2:38][C:39]2([CH3:44])[CH2:43][CH2:42][CH2:41][CH2:40]2)[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(CC)C(C)C)(C)C>ClCCl.C(OCC)(=O)C>[C:5]([O:9][C:10]([N:12]1[C@@H:17]([C@@H:18]([OH:36])[C@@H:19]([NH:35][C:1](=[O:3])[CH3:2])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:22]=2)[CH2:16][O:15][C@@H:14]([O:37][CH2:38][C:39]2([CH3:44])[CH2:40][CH2:41][CH2:42][CH2:43]2)[CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 68564333HCID 68564333, compound

Product 1

HCID 68561840(2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methyl-cyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl esterYield 25%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add acetyl chloride (0.13 mL, 1.82 mmol) to an ice cold solution of (2R,5R)-5-[2-amino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester (0.91 g, 1.652 mmol) and N,N-diisopropyl-ethylamine (0.58 mL, 3.30 mmol) in dichloromethane (20 mL). Stir 15 minutes and dilute with ethyl acetate and wash with 1 N hydrochloric acid, saturated aqueous sodium chloride, dry (magnesium sulfate) and purify (silica gel chromatography, elutin with dichloromethane/ethyl acetate) to give the desired compound (246 mg).

Workup

  1. washwash with 1 N hydrochloric acid, saturated aqueous sodium chloride
  2. dry with materialdry (magnesium sulfate)
  3. custompurify (silica gel chromatography, elutin with dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-b60a1c936d55443c9e11999a26e58356
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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