1,2-Dichloro-1,1-difluoroethane → N-Boc-S-(2-chloro-1,1-difluoroethyl)-D,L-homocysteine

HRID 1698885

Reaction equation

[C:1]([NH:8][CH:9]([C:13]([OH:15])=[O:14])[CH2:10][CH2:11][SH:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[C:17]([F:21])([F:20])[CH2:18][Cl:19]>[OH-].[Na+].CN(C=O)C>[C:1]([NH:8][CH:9]([C:13]([OH:15])=[O:14])[CH2:10][CH2:11][S:12][C:17]([F:21])([F:20])[CH2:18][Cl:19])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Conditions

Temperature: 50 °C

Procedure

Ex-18a) A solution of N-Boc-D,L-homocysteine (5 mmol) in NaOH (5 mL, 2N) was slowly added to a stirred solution of 1,2-dichloro-1,1-difluoroethane (5 mmol) in DMF. The resulting solution was then warmed to 50° C. for 16 hours. The reaction solution was then poured onto EtOAc and extracted with citric acid (5%) and brine, dried (Na2SO4) and concentrated in vacuo. The material was purified by flash column chromatography to yield N-Boc-S-(2-chloro-1,1-difluoroethyl)-D,L-homocysteine. Example 18 is prepared in the same manner as described for Example 17 starting with N-Boc-S-(2-chloro-1,1-difluoroethyl)-D,L-homocysteine.

Workup

additionThe reaction solution was then poured onto EtOAc
extractionextracted with citric acid (5%) and brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe material was purified by flash column chromatography

Sources & evidence

ORD record: ord-150efa6fd236480789542d590f9ef718
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06344483B1

Linked notes

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