Benzyl chloroformate → (2S)-4-[[3-carboxy-3-(phenylmethoxycarbonylamino)propyl]disulfanyl]-2-(phenylmethoxycarbonylamino)butanoic acid

HRID 714016Notes

Reaction equation

[CH2:1]([S:8][S:9][CH2:10][CH2:11][C@H:12]([NH2:16])[C:13]([OH:15])=[O:14])[CH2:2][C@H:3]([NH2:7])[C:4]([OH:6])=[O:5].[OH-:17].[Na+].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>C1COCC1>[S:8]([CH2:1][CH2:2][CH:3]([NH:7][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:17])[C:4]([OH:6])=[O:5])[S:9][CH2:10][CH2:11][CH:12]([NH:16][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C:13]([OH:15])=[O:14]

Participants

Conditions

Temperature: 7.5 °C

Procedure

L-Homocystine (200.0 g, 745.5 mmol, 1.0 eq.) is suspended in THF (1000 mL, 5.0 vol.) and cooled to 5-10° C. Addition of 20% sodium hydroxide (521.7 mL, 626.2 g, 125.25 g at 100%, 3.13 mmol, 4.2 eq.) is followed by addition of benzyl chloroformate (220.3 mL, 267 g, 1565.5 mmol, 2.1 eq.). Conversion is complete after a night at room temperature (L-Homocystine<1%). Extractions and washings of the organic layer with water leads to a yellow oil which is isolated in quantitative yield, and which slowly crystallizes as a yellowish solid at room temperature.

Workup

waitConversion is complete after a night at room temperature
extractionExtractions and washings of the organic layer with water leads to a yellow oil which
customis isolated in quantitative yield, and which
customslowly crystallizes as a yellowish solid at room temperature

Sources & evidence

ORD record: ord-cf52fe979e6d4477b0e71a7d37f5c82b
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187418B2

Reaction notes

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