Lithium hydroxide, monohydrate → HCID 53884484, compound

HRID 862245Notes

Reaction equation

HRID 862245 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][N:5]1[C:11](=[O:12])[C@@H:10]([NH:13][C:14](=[O:23])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9][NH:8][C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]1=2.O.[OH-].[Li+]>CO.O>[C:17]1([CH2:16][CH2:15][C:14]([NH:13][C@@H:10]2[C:11](=[O:12])[N:5]([CH2:4][C:3]([OH:28])=[O:2])[C:6]3[CH:27]=[CH:26][CH:25]=[CH:24][C:7]=3[NH:8][CH2:9]2)=[O:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53730563HCID 53730563, compound

Product 1

HCID 53884484HCID 53884484, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(3(S)-(3-Phenylpropionylamino)-2-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)acetic acid methyl ester (104a) was dissolved in 90% methanol. Lithium hydroxide hydrate was added to the reaction and the reaction was stirred at room temperature for 4 h. The reaction was evaporated in vacuo to give a white solid. This was dissolved in 20 ml of water and acidified to pH 5 and extracted with ethyl acetate to afford 304 mg (88%) of the title compound as a white solid. 1H NMR (CDCl3) δ 7.5-6.9 (11H, m), 4.92-4.8 (1H, m), 4.7-4.58 (1H, d), 4.38-4.25 (1H, d), 3.88-3.78 (1H, m), 3.45-3.25 (1H, m), 3.05-2.85 (2H, m), 2.55-2.45 (2H, m).

Workup

  1. customThe reaction was evaporated in vacuo
  2. customto give a white solid
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-11acdec1a3ff4614aad967b30512cb74
Source dataset
uspto-grants-1998_02
Patent number
US05716929

Reaction notes

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