Acetic Acid → HCID 18597320, compound

HRID 1980836Notes

Reaction equation

HRID 1980836 reaction equation
[CH2:1]([NH:5][C:6](=[O:25])[C@H:7]([CH3:24])[NH:8][C:9](=[O:23])[C@@H:10]([NH:16][C@@H:17]([C:19]([O:21]C)=[O:20])[CH3:18])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].C(O)(=O)C>CO>[CH2:1]([NH:5][C:6](=[O:25])[C@H:7]([CH3:24])[NH:8][C:9](=[O:23])[C@@H:10]([NH:16][C@@H:17]([C:19]([OH:21])=[O:20])[CH3:18])[CH2:11][C:12]([CH3:15])([CH3:13])[CH3:14])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 18597321HCID 18597321, compound

Product 1

HCID 18597320HCID 18597320, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-[2-(S)-N(1-(R)-Methoxycarbonylethyl)amino-4,4-dimethylpentanoyl]-L-alanine N-butylamide (65 mg) in methanol (30 ml) was treated with IN-sodium hydroxide (3 ml) at 20° for 6 h. Excess acetic acid was then added and the solvent evaporated in vacuo. The residue was chromatographed on reverse phase silica (RF 18) in a gradient of 20%-80% methanol in water. Elution in 70% methanol in water afforded the title compound (30 mg) as a freeze-dried powder, m.p. 137°-138°; (Found: [m+1]+ =344.2548. C17H34N3O4 requires [m+1]+ =344.2549); δ(D2O) 0.9 (3H,t,J=6 Hz,CH2CH3); 0.94 (9H,s,C(CH3)3); 1.2-1.8 (6H,m,(CH2)2 and CH2); 1.4 (3H,d,J=8 Hz,CH3); 1.52 (3H,d,J=7 Hz,CH 3); 3.18 (2H,t,J=6 Hz,NHCH2); 3.66 (1H,q,J=5 Hz,CHCO); 3.88 (1H,d,J=10 Hz,CHCH2) and 4.38 (1H,q,J=5 Hz,CHCH3).

Workup

  1. customthe solvent evaporated in vacuo
  2. customThe residue was chromatographed on reverse phase silica (RF 18) in a gradient of 20%-80% methanol in water
  3. washElution in 70% methanol in water

Sources & evidence

ORD record
ord-3de018e77348433b986d0fe3c86c8b2a
Source dataset
uspto-grants-1985_04
Patent number
US04511504

Reaction notes

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