HCID 54349977, compound → HCID 9826986, compound

HRID 277202Notes

Reaction equation

HRID 277202 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH2:5][C:6]1[S:10][C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16](=[O:35])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[O:26])=[CH:20][CH:19]=2)=[N:8][CH:7]=1>CO.O1CCCC1.[OH-].[Li+]>[C:29]1([CH3:34])[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[NH:27][C:25](=[O:26])[NH:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][C:16]([N:12]2[CH2:13][CH2:14][CH2:15][CH:11]2[C:9]2[S:10][C:6]([CH2:5][CH2:4][C:3]([OH:36])=[O:2])=[CH:7][N:8]=2)=[O:35])=[CH:23][CH:22]=1

Participants

5

Reactant 1

HCID 54349977HCID 54349977, compound

Product 1

HCID 9826986HCID 9826986, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution was prepared of 3-[2-(1-{[4-(3-o-Tolyl-ureido)-phenyl]-acetyl}-pyrrolidin-2-yl)-thiazol-5-yl]-propionic acid methyl ester (0.33 g, 0.65 mmol) in methanol (4 mL), tetrahydrofuran (8 mL) and aqueous lithium hydroxide (2M, 4 mL). The solution was stirred for 4 h and partitioned between aqueous hydrochloric acid (1N, 30 mL) and ethyl acetate (100 mL). The aqueous portion was extracted with ethyl acetate (50 mL). The combined organic portions were extracted with brine (20 mL) and the solvent removed in vacuo to give the title compound (0.3 g, 94%). 1HNMR (400 MHz, CD3OD): δ7.60 (d, J=7.3 Hz, 1H), 7.46 (s, 0.3H), 7.39 (d, J=8.5 Hz, 2.7H), 7.29 (d, J=8.5 Hz, 0.6), 7.18 (m, 3H), 6.99 (m, 1.4H), 5.40 (d, J=7.0 Hz, 0.3H), 5.34 (d, J=6.0 Hz, 0.7H) 3.4-3.8 (m, 4H), 3.05 (m, 2H), 2.60 (m, 2H), 2.27 (s, 3H), 1.9-2.2 (m, 4H). MS: Calc'd for C25H26N4O4S: 492.18. Found: (M+1) 492.9.

Workup

  1. custompartitioned between aqueous hydrochloric acid (1N, 30 mL) and ethyl acetate (100 mL)
  2. extractionThe aqueous portion was extracted with ethyl acetate (50 mL)
  3. extractionThe combined organic portions were extracted with brine (20 mL)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9cfe872136d7495983e16b109d7d7682
Source dataset
uspto-grants-2002_03
Patent number
US06355662B1

Reaction notes

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