Water → HCID 22858518, compound

HRID 375987Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@@H:13]([OH:18])[C:14]([O:16][CH3:17])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35].O>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C@@H:13]([O:18][S:34]([CH3:33])(=[O:36])=[O:35])[C:14]([O:16][CH3:17])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -10 °C

Procedure

206 g of methyl N-benzyloxycarbonyl-3(S)-amino-2(R)-hydroxy-4-phenylbutyrate was dissolved in 1,000 ml of methylene chloride and cooled to -10° C. After adding 79 g of triethylamine, 82.5 g of methanesulfonyl chloride was slowly added thereto under cooling at the same temperature. The obtained mixture was stirred at 15° to 0° C. for 1 hour and then 500 ml of water was added thereto to effect liquid/liquid separation. The organic layer was separated and washed successively with 1N hydrochloric acid, a 5% aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and concentrated under reduced pressure. Thus 253 g of methyl N-benzyloxycarbonyl-3(S)-amino-2(R)-methanesulfonyloxy-4-phenylbutyrate was obtained as a pale yellow, oily substance.

Workup

additionwas slowly added
temperatureunder cooling at the same temperature
customliquid/liquid separation
customThe organic layer was separated
washwashed successively with 1N hydrochloric acid
concentrationa 5% aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and concentrated under reduced pressure

Sources & evidence

ORD record: ord-f053192a0fe6454a94525b83f7a48473
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488118

Reaction notes

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