Sodium Hydroxide → HCID 21710801, compound

HRID 651167Notes

Reaction equation

HRID 651167 reaction equation
C[O:2][C:3]([CH:5]1[N:9]([C:10](=[O:25])[CH2:11][NH:12][C:13]([C:15]2[NH:16][C:17]3[C:22]([CH:23]=2)=[CH:21][C:20]([Cl:24])=[CH:19][CH:18]=3)=[O:14])[CH2:8][CH2:7][S:6]1)=[O:4].[OH-].[Na+]>CO>[Cl:24][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:13]([NH:12][CH2:11][C:10]([N:9]1[CH2:8][CH2:7][S:6][CH:5]1[C:3]([OH:4])=[O:2])=[O:25])=[O:14])=[CH:23]2

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 53941519HCID 53941519, compound

Product 1

HCID 21710801HCID 21710801, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-{[(5-chloro-1H-indole-2-carbonyl)-amino]-acetyl}-thiazolidine2-carboxylic acid methyl ester (196 mg, 0.5 mmol) in methanol (10 mL) was treated with aqueous 1 N NaOH (0.5 mL) at 25° C. After 3 hours, more 1 N NaOH (0.25 mL) was added. The mixture was stirred at 25° C. overnight, concentrated, the residue stirred with ethyl acetate (30 mL) and 1 N NaOH (5 mL), and the resulting mixture acidified to pH 1.8 with aqueous 6 N HCl. The aqueous layer was separated and extracted with ethyl acetate. The organic layers were combined, dried, and concentrated giving a solid which was triturated with 1:1 ether-hexane and dried. Yield 186 mg, 99%; HPLC (60/40) 3.13 minutes (98%); TSPMS 368/370 (MH+, 70%), 339 (100%).

Workup

  1. concentrationconcentrated
  2. stirringthe residue stirred with ethyl acetate (30 mL) and 1 N NaOH (5 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated
  7. customgiving a solid which
  8. customwas triturated with 1:1 ether-hexane
  9. customdried
  10. customHPLC (60/40) 3.13 minutes (98%)

Sources & evidence

ORD record
ord-ec233547fd344e85acbc2636a9f44c55
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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