Benzyl chloroformate → HCID 86621459, compound

HRID 416524Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][S:4]([OH:7])(=[O:6])=[O:5].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>>[CH2:10]([O:9][CH2:8][C@H:2]([NH:1][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[CH2:3][S:4]([OH:7])(=[O:6])=[O:5])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 10387Benzyl chloroformate

HCID 14427206HCID 14427206, compound

Product 1

HCID 86621459HCID 86621459, compound

Procedure

(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propane-1-sulfonic acid was prepared by an analogous procedure as described in example 26 iv) starting from 1.76 g (7.19 mmol) (S)-2-amino-3-benzyloxy-propane-1-sulfonic acid and 1.16 ml (1.1 equiv.) benzyl chloroformate. Final purification by preparative RP-HPLC CH3CN/H2O gradient+0.1% TFA) gave pure (S)-3-benzyloxy-2-benzyloxycarbonylamino-propane-1-sulfonic acid as a colorless oil.

Workup

custom(S)-3-Benzyloxy-2-benzyloxycarbonylamino-propane-1-sulfonic acid was prepared by an analogous procedure
customFinal purification by preparative RP-HPLC CH3CN/H2O gradient+0.1% TFA)

Sources & evidence

ORD record: ord-690f3a542a874c5894e67c5402da3e52
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088925B2

Reaction notes

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