Water → HCID 44311701, compound

HRID 1957037Notes

Reaction equation

HRID 1957037 reaction equation
C[O:2][C:3](=[O:43])[C@H:4]([CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)[NH:5][C:6](=[O:32])[C@@H:7]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][N:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[N:8]([C:10](=[O:19])[C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[CH:12]=1)[CH3:9].O.[OH-].[Li+].O>CO.O1CCCC1>[CH3:18][C:13]1[CH:12]=[C:11]([CH:16]=[C:15]([CH3:17])[CH:14]=1)[C:10]([N:8]([CH3:9])[C@@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:43])=[O:2])[CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)=[O:32])[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[O:31][N:30]=[CH:29][CH:28]=2)=[CH:25][CH:26]=1)=[O:19]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 70094113HCID 70094113, compound

Product 1

HCID 44311701HCID 44311701, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

[N-(3,5-dimethylbenzoyl)-N-methyl-3-[4-(5-isoxazolyl)-phenyl]-(D)-alanyl]-(L)-tryptophane methyl ester (50 mg) is treated with lithiumhydroxide monohydrate (3.8 mg) in methanol (1 ml), tetrahydrofurane (0.5 ml), and water (0.5 ml), at 0° C. for 1 hour, and at room temperature for 2 hours. The mixture is then partitioned between water and ether, the water phase acidified with 1N hydrochloric acid, and subsequently extracted with ethyl acetate. The ethyl acetate phase is washed with brine, dried, and evaporated to give [N-(3,5-dimethylbenzoyl)-N-methyl-3-[4-(5-isoxazolyl)-phenyl]-(D)-alanyl]-(L)-tryptophane. NMR (CDCl3, 400 MHz) δ [ppm] 8.29 (s), 8.12 (s), 7.70 (m), 7.55 (m), 7.28 (m), 7.17 (m), 7.07 (m), 6.98 (m), 6.86 (m), 6,61 (s), 6.53 (s), 6.49 (s), 5.97 (s), 5.43 (m), 4.87 (m), 4.40 (m), 3.90 (m), 3.33 (m), 2.08 (m), 2.77 (s), 2.18 (s), 1.89 (s).

Workup

  1. customThe mixture is then partitioned between water and ether
  2. extractionsubsequently extracted with ethyl acetate
  3. washThe ethyl acetate phase is washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-a68c2e66c79b420686c32353a474264f
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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