Hydrochloric Acid → HCID 67353694, compound

HRID 75818Notes

Reaction equation

HRID 75818 reaction equation
C[O:2][C:3](=[O:33])[CH:4]([NH:8][C:9]([C:11]1[O:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])=[O:24])=[CH:18][CH:17]=2)[CH:12]=1)=[O:10])[CH:5]([CH3:7])[CH3:6].[Li+].[OH-].Cl>C1COCC1>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:25][C:23](=[O:24])[NH:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[CH:12]=[C:11]([C:9]([NH:8][CH:4]([CH:5]([CH3:6])[CH3:7])[C:3]([OH:33])=[O:2])=[O:10])[O:15][N:14]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 673524222-[(3-{4-[3-(2-Fluoro-phenyl)ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-3-methyl-butyric acid methyl ester

Product 1

HCID 67353694HCID 67353694, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[(3-{4-[3-(2-Fluoro-phenyl)ureido]-phenyl}-isoxazole-5-carbonyl)-amino]-3-methyl-butyric acid methyl ester (800 mg) was dissolved in THF (20 ml). 1M aqueous LiOH solution (3.52 ml) was added and stirred at RT for 14 h. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. Organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to get off white solid which was crystallized from EtOAc to yield 490 mg (63%) white solid. MS (ES+): m/z 441 (M+1); 1HNMR (DMSO-d6, 300 MHz): δ 12.83 (bs, 1H), 9.34 (s, 1H), 8.95 (d, 1H), 8.63 (s, 1H), 8.13 (m, 1H), 7.85 (d, 2H), 7.68 (s, 1H), 7.62 (d, 2H), 7.24 (m, 1H), 7.14 (m, 1H), 7.02 (m, 1H), 4.26 (m, 1H), 2.21 (m, 1H), 0.95 (dd, 6H).

Workup

  1. extractionextracted with EtOAc
  2. customOrganic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get off white solid which
  6. customwas crystallized from EtOAc

Sources & evidence

ORD record
ord-e01872e5c2c04eb2b140933f6eb132e3
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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