Acetic Acid → HCID 18597298, compound

HRID 1980831Notes

Reaction equation

HRID 1980831 reaction equation
[CH3:1][NH:2][C:3](=[O:32])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[NH:5][C:6](=[O:22])[C@H:7]([CH2:18][CH:19]([CH3:21])[CH3:20])[NH:8][C@@H:9]([C:14]([O:16]C)=[O:15])[CH2:10][CH2:11][S:12][CH3:13].O.CC(O)=O>CO.[OH-].[Na+]>[CH3:1][NH:2][C:3](=[O:32])[C@H:4]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[NH:5][C:6](=[O:22])[C@H:7]([CH2:18][CH:19]([CH3:20])[CH3:21])[NH:8][C@@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH2:11][S:12][CH3:13]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 18597308HCID 18597308, compound

Product 1

HCID 18597298HCID 18597298, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

N[1-(R)-Carbomethoxy-3-methylthiopropyl]-L-leucyl-O-methyl-L-tyrosine N-methylamide (100 mg, 0.2 mM) was dissolved in MeOH (10 ml) and treated with IN NaOH (0.25 ml, 0.25 mM). After 18 h another portion of IN NaOH (0.5 ml, 0.5 mM) and H2O (2 ml) were added. After a further 18 h the reaction mixture was acidified with AcOH and evaporated in vacuo. The resulting white solid was chromatographed on C18 -Silica eluting with a gradient of 10% to 40% MeOH in H2O. The relevant fractions were pooled and evaporated in vacuo; the residue was recrystallised from hot H2O to yield the title compound (20 mg); m.p. 170-180; (Found: C,56.88; H,7.49; N,9.05; calculated for C22H35N3O5S,.0.6H2O: C,56.90; H,7.86; N,9.0 5%); νmax (Nujol) 3340, 1650 and 1625 cm-1 ; δ(d6DMSO) 0.82 (6H,t,J=7 Hz, (CH3)2CH), 1.17 and 1.5-1.9 (5H,m, CH2CH(CH3)2 and SCH2CH2), 2.04 (3H,s,CH3S), 2.3 (2H,m,--SCH2), 2.6 (3H,d,J=5 Hz, NHCH3), 2.6-2.95 (3H,m,CH2C6H4 and α--CH),), 3.14 (1H,t,J=7 Hz,α--CH), 3.7 (3H,s,OCH3), 4.25 (1H,m, --CH), 6.8 and 7.12 (2×2H, each d, each J=9 Hz,C6H4), 7.88 (1H,q,J=5 Hz, NHCH3) and 8.18 (1H,d,J=9 Hz, NHCH); m/e 454 (100%, [m+1]+).

Workup

  1. customevaporated in vacuo
  2. customThe resulting white solid was chromatographed on C18 -Silica eluting with a gradient of 10% to 40% MeOH in H2O
  3. customevaporated in vacuo
  4. customthe residue was recrystallised from hot H2O

Sources & evidence

ORD record
ord-b12d35f6b4c548d09f9e874c69e31887
Source dataset
uspto-grants-1985_04
Patent number
US04511504

Reaction notes

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