Hydrochloric Acid → HCID 67353499, compound

HRID 75854Notes

Reaction equation

HRID 75854 reaction equation
[OH:1][C@H:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:16]=[C:15]([C:17]([NH:19][CH:20]([CH:25]([CH3:27])[CH3:26])[C:21]([O:23]C)=[O:22])=[O:18])[O:14][N:13]=2)=[CH:8][CH:7]=1)=[O:4].O.[OH-].[Li+].Cl>C1COCC1>[OH:1][C@H:2]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:16]=[C:15]([C:17]([NH:19][CH:20]([CH:25]([CH3:26])[CH3:27])[C:21]([OH:23])=[O:22])=[O:18])[O:14][N:13]=2)=[CH:10][CH:11]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67353472Methyl 2-(3-(4-((R)-2-hydroxy-2-phenylacetamido)phenyl) isoxazole-5-carboxamido)-3-methylbutanoate

Product 1

HCID 67353499HCID 67353499, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To Methyl 2-(3-(4-((R)-2-hydroxy-2-phenylacetamido)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate (135 mg) in THF (4 ml) 1 M aqueous solution of Lithium hydroxide monohydrate (0.6 ml) was added and reaction mixture was stirred at RT for 6 hours. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. Organic layer was collected and dried over Na2SO4 and concentrated to obtain off white solid, which was crystallized from EtOAc to obtain the title compound as white solid. Yield: 80 mg (61%); MS (ES+): m/z 438 (M+1); 1HNMR (DMSO-d6; 300 MHz): δ 12.86 (bs, 1H), 10.2 (s, NH), 8.97 (d, 1H), 7.88 (d, 4H), 7.7 (s, 1H), 7.54 (m, 2H), 7.39-7.29 (m, 3H), 6.51 (d, 1H), 5.13 (d, 1H), 4.27 (m, 1H), 2.19 (m, 1H), 0.97 (d, 6H).

Workup

  1. customreaction mixture
  2. extractionextracted with EtOAc
  3. customOrganic layer was collected
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto obtain off white solid, which
  7. customwas crystallized from EtOAc

Sources & evidence

ORD record
ord-ce4429babe5b45fbb9cf70b41c5060c6
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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