Hydrochloric Acid → HCID 53869768, compound

HRID 615352Notes

Reaction equation

HRID 615352 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@H:9]([C:10]([OH:12])=[O:11])[CH2:8][S:7][CH:6]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])=[O:4].[NH2:20][CH2:21][C:22]([OH:24])=[O:23].Cl>[OH-].[Na+]>[C:22]([CH2:21][NH:20][CH2:2][C:3]([N:5]1[C@H:9]([C:10]([OH:12])=[O:11])[CH2:8][S:7][CH:6]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])=[O:4])([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 750GlycineHCID 53866484HCID 53866484, compound

Product 1

HCID 53869768HCID 53869768, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

(4R)-3-Chloroacetyl-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid (6 g) was added to a stirred solution of glycine (1.5 g) in N sodium hydroxide (80 ml), and stirred overnight at room temperature. The solution was adjusted to pH 1.5 by 20% hydrochloric acid and washed with ethyl acetate. The aqueous layer was adjusted to pH 3.2, and the separated crystals were collected by filtration to 3.28 g (48.2%) of the titled compound: mp 181°-182° C. (dec.) (water); [α]D24 +271.2° (c=0.5, N--NaOH). IR (KBr, cm-1): 3400, 3200, 1740, 1672, 1560, 1440, 1380, 1335, 1212, 752, 648, NMR (K2CO3 in D2O, δ): 3.0-4.3 (6H, m, C5 --H, COCH2NHCH2CO2H), 6.33 and 6.43 (1H, each s, C2 --H), 6.6-7.3 (3H, m, arom. H), 7.82 (1H, br. d, J=8 Hz, arom. H), 9.0-10.3 (2H, br. s, --OH, --CO2H).

Workup

  1. washwashed with ethyl acetate
  2. filtrationthe separated crystals were collected by filtration to 3.28 g (48.2%) of the titled compound

Sources & evidence

ORD record
ord-ac9daa44a60b441499210e708e6ada1e
Source dataset
uspto-grants-1985_02
Patent number
US04499102

Reaction notes

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