Hydrochloric Acid → HCID 86751599, compound

HRID 2293794Notes

Reaction equation

HRID 2293794 reaction equation
[ClH:1].[NH2:2][C@@H:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1F)[C@H:4]([SH:9])[C:5]([O:7][CH3:8])=[O:6].C(OC(N[C@@H](C1C=CC=CC=1F)C(S)C(OC)=O)=O)(C)(C)C.Cl>C(OCC)(=O)C>[ClH:1].[NH2:2][C@@H:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C@H:4]([SH:9])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 57101435HCID 57101435, compoundHCID 86751600HCID 86751600, compound

Product 1

HCID 86751599HCID 86751599, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl (2S,3S) 3-amino-2-mercapto-3-(2-fluorophenyl)propionate hydrochloride may be prepared in a similar manner to that described in Example 1E, but starting with 8.2 g of methyl (2RS,3S)-3-tert-butoxycarbonylamino-2-mercapto-3-(2-fluorophenyl)propionate and 20 ml of a methanolic 5N solution of hydrochloric acid. Stirring is continued for 3 h at a temperature in the region of 20° C. and the reaction medium is then concentrated to dryness under reduced pressure at 30° C. The residue obtained is beaten in 20 ml of ethyl acetate. The solid obtained is separated out by filtration and air-dried. 2.3 g of methyl (2S,3S) 3-amino-2-mercapto-3-phenylpropionate hydrochloride are thus obtained in the form of a white solid melting at 172° C. After evaporation of the filtrate, 1.8 g of methyl (2RS,3S)-3-amino-2-mercapto-3-phenylpropionate hydrochloride are also isolated, in the form of a white solid which is used without further purification in the subsequent syntheses.

Workup

  1. concentrationthe reaction medium is then concentrated to dryness under reduced pressure at 30° C
  2. customThe residue obtained
  3. customThe solid obtained
  4. customis separated out by filtration
  5. customair-dried

Sources & evidence

ORD record
ord-b2af0761ee8946f8b88cbf192b2c7549
Source dataset
uspto-grants-1997_11
Patent number
US05686622

Reaction notes

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