Acetic Acid → HCID 18597309, compound

HRID 1980828Notes

Reaction equation

HRID 1980828 reaction equation
[CH2:1]([NH:9][C:10](=[O:24])[C@H:11]([CH2:20][CH:21]([CH3:23])[CH3:22])[NH:12][C@@H:13]([C:15]([O:17]CC)=[O:16])[CH3:14])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(O)=O>CO.[OH-].[Na+]>[CH2:1]([NH:9][C:10](=[O:24])[C@H:11]([CH2:20][CH:21]([CH3:23])[CH3:22])[NH:12][C@@H:13]([C:15]([OH:17])=[O:16])[CH3:14])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 18597314HCID 18597314, compound

Product 1

HCID 18597309HCID 18597309, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

N[1-(R)-Ethoxycarbonylethyl]-L-Leucine N-phenethylamide (710 mg, 2.1 mM) was dissolved in MeOH (50 ml) and treated with IN NaOH (3 ml, 3 mM) at room temperature. After 12 h, the reaction mixture was acidified with AcOH and evaporated in vacuo to a solid which was washed with H2O and dried to yield the title compound (400 mg); m.p. 201°-205°; (Found: C,66.44; H,8.55; N,9.11; C17H26N2O3 requires C,66.64; H,8.55; N,9.14%); νmax (Nujol) 3330, 1660 and 1530 cm-1 ; δ(d6DMSO) 0.825 (6H,t,J=6.2 Hz, (CH3)2CH), 1.15 (3H,d, J=6.8 Hz, CH3CH), 1.29 (2H,m,CH2CH), 1.55 (1H, heptet,J=7 Hz, CH(CH3)2), 2.71 (2H,t,J=7 Hz, CH2C6H5), 3.0 (1H,q,J=7 Hz, CHCH3), 3.14 (1H,t,J=7 Hz, α--CH), 3.32 (2H,q,J=6 Hz, NHCH2CH2), 7.12 (5H,m,C6H5), 7.5 (2H,br s, OH and CHNHCH) and 8.15 (2H,t,J=5 Hz, NHCH2).

Workup

  1. customevaporated in vacuo to a solid which
  2. washwas washed with H2O
  3. customdried

Sources & evidence

ORD record
ord-5c7bc00489ec453ab4a7b4750ef18dba
Source dataset
uspto-grants-1985_04
Patent number
US04511504

Reaction notes

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