Hydrochloric Acid → HCID 18793923, compound

HRID 1003959Notes

Reaction equation

HRID 1003959 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][N:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27])[C:6](=[O:20])[CH:7]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][S:9]C(=O)C.[S-2].[Na+].[Na+].Cl>CO.O>[CH2:13]([CH:7]([CH2:8][SH:9])[C:6]([N:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27])[CH2:4][C:3]([OH:28])=[O:2])=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14804Sodium SulfideHCID 18793882HCID 18793882, compound

Product 1

HCID 18793923HCID 18793923, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of the N-(S-acetyl-2'-benzyl-3'-mercaptopropionyl)-2-fluorophenylglycine methyl ester of Example 19b (0.2 mmol) in methanol (2 ml) was degassed with argon for 20 minutes then treated with a solution of sodium sulphide (1 mmol) in degassed water (2 ml). After 30-90 minutes, 0.25M aq. HCl (20 ml) was introduced and the mixture extracted with ethyl acetate (3×20 ml). The dried (MgSO4) organic phases were evaporated to give the title compound as a clear oil, an approximately equimolar mixture of diastereoisomers.

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×20 ml)
  2. dry with materialThe dried (MgSO4) organic phases
  3. customwere evaporated

Sources & evidence

ORD record
ord-711fef172413439a9626968bd63218a9
Source dataset
uspto-grants-2000_04
Patent number
US06048852

Reaction notes

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