Hydrochloric Acid → HCID 53698428, compound

HRID 615350Notes

Reaction equation

HRID 615350 reaction equation
C[O:2][C:3]([CH2:5][CH:6]([CH3:24])[C:7]([N:9]1[C@H:13]([C:14]([OH:16])=[O:15])[CH2:12][S:11][CH:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=[O:8])=[O:4].Cl>[OH-].[Na+]>[C:3]([CH2:5][CH:6]([CH3:24])[C:7]([N:9]1[C@H:13]([C:14]([OH:16])=[O:15])[CH2:12][S:11][CH:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23])=[O:8])([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54418248HCID 54418248, compound2×

Product 1

HCID 53698428HCID 53698428, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

(4R)-3-[3-(Methoxycarbonyl)-2-methylpropanoyl]-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid (compound 4) (7.1 g) was dissolved in 2N sodium hydroxide (40 ml) and stirred for 1 hour at room temperature. The resulting solution was acidified with dilute hydrochloric acid and the separated crystals were filtered to give 5.1 g (75%) of the titled compound: mp 163°-164° C. (dec.) (ethyl acetate); [α]D25 +174.1° (c=1.0, methanol). IR (nujol, cm-1): 3330 (OH), 1730 and 1710 (COOH), 1629 (CON), 1280, 1234, 856, 771.

Workup

  1. filtrationthe separated crystals were filtered

Sources & evidence

ORD record
ord-bfaa2c64f3aa48b4848b7993148678ec
Source dataset
uspto-grants-1985_02
Patent number
US04499102

Reaction notes

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