Sodium Hydroxide → 3-[4-(2-{4-[(2,3-Dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyric acid

HRID 1167807Notes

Reaction equation

HRID 1167807 reaction equation
[N:1]1([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([C@H:29]([CH3:36])[CH2:30][C:31]([O:33]CC)=[O:32])=[CH:25][CH:24]=3)=[O:21])=[CH:15][C:14]=2[O:37][CH3:38])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C.O>[N:1]1([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([CH:29]([CH3:36])[CH2:30][C:31]([OH:33])=[O:32])=[CH:27][CH:28]=3)=[O:21])=[CH:15][C:14]=2[O:37][CH3:38])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86585371ethyl (R) 3-[4-(2-{4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyrate

Product 1

HCID 98700693-[4-(2-{4-[(2,3-Dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyric acidYield 86.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of ethyl (R) 3-[4-(2-{4-[(2,3-dihydro-indole-1-carbonyl)-amino]-3-methoxy-phenyl}-acetylamino)-phenyl]-butyrate (1.3 g, Reference Example 4) in ethanol (40 mL) and water (15 mL) was treated with sodium hydroxide (5 mL, 1M). After stirring at 50° C. for 3 hours the mixture was evaporated to low bulk and then acidified with hydrochloric acid (1M). The resulting white precipitate was filtered, then washed with water, then with ether, and then dried to give the title compound (1.06 g) as a white powder. HPLC: RT=15.3 minutes (>95% by ELS). MS(ES+): 488(MH+); MS(ES−): 486(M−).

Workup

  1. customwas evaporated to low bulk
  2. filtrationThe resulting white precipitate was filtered
  3. washwashed with water
  4. dry with materialwith ether, and then dried

Sources & evidence

ORD record
ord-c0cb1b008f944476a6436b4577511ee2
Source dataset
uspto-grants-2003_09
Patent number
US06620832B2

Reaction notes

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