Dimethylformamide → HCID 68127027, compound

HRID 1657354Notes

Reaction equation

HRID 1657354 reaction equation
[CH2:1]([S:8][CH2:9][C@@H:10]([C:12]([N:14]1[CH2:33][CH2:32][CH2:31][C@H:15]1[C:16]([NH:18][C@H:19]([C:24]([NH:26][CH2:27][C:28]([NH2:30])=[O:29])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])=[O:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=CC([O:43][C:44](=O)[C@H:45]([CH2:57][C:58](=[O:60])[NH2:59])[NH:46]C(OCC2C=CC=CC=2)=O)=CC=1)([O-])=O.CN(C)C=O>C(OCC)(=O)C>[NH2:46][C@H:45]([C:44]([NH:11][C@H:10]([C:12]([N:14]1[CH2:33][CH2:32][CH2:31][C@H:15]1[C:16]([NH:18][C@H:19]([C:24]([NH:26][CH2:27][C:28]([NH2:30])=[O:29])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:17])=[O:13])[CH2:9][S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:43])[CH2:57][C:58](=[O:60])[NH2:59]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7021351Z-Asn-onpHCID 21141077HCID 21141077, compound

Product 1

HCID 68127027HCID 68127027, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of S-benzyl-L-cysteinyl-L-prolyl-L-leucyl-glycinamide (0.502 g.) in ethyl acetate (3 ml.) benzyloxycarbonyl-L-asparagine p-nitrophenyl ester (0.387 g., 1.0 mmol) was added and the suspension stirred at room temperature for 48 hr. The precipitate which formed was collected by filtration and washed with ethyl acetate (20 ml.) and ethanol (5 ml.), and then dried. The crude benzyloxycarbonyl-L-asparaginyl-S-benzyl-L-cysteinyl-L-prolyl-L-leucyl-glycinamide was recrystallized from 40% methanol. Yield, 0.718 g. (99%); m.p. 212°- 213.5°; [α]20D -60.5° (c 1, dimethylformamide).

Workup

  1. customThe precipitate which formed
  2. filtrationwas collected by filtration
  3. washwashed with ethyl acetate (20 ml.) and ethanol (5 ml.)
  4. customdried
  5. customThe crude benzyloxycarbonyl-L-asparaginyl-S-benzyl-L-cysteinyl-L-prolyl-L-leucyl-glycinamide was recrystallized from 40% methanol
  6. customYield

Sources & evidence

ORD record
ord-0f0ea307e9d844a69ae9303acbe48824
Source dataset
uspto-grants-1976_06
Patent number
US03960828

Reaction notes

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