Ammonia → Nalpha-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-D-tyrosyl-D-alaninamide

HRID 437691Notes

Reaction equation

HRID 437691 reaction equation
C[O:2][C:3](=O)[C@@H:4]([CH3:59])[NH:5][C:6](=[O:58])[C@@H:7]([CH2:43][C:44]1[CH:49]=[CH:48][C:47]([O:50][CH2:51]C2C=CC=CC=2)=[CH:46][CH:45]=1)[NH:8][C:9](=[O:42])[C@H:10]([CH2:33][O:34][CH2:35]C1C=CC=CC=1)[NH:11][C:12](=[O:32])[C@H:13]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[NH3:61].CO>>[C:18]([O:17][C:15]([NH:14][C@H:13]([C:12]([NH:11][C@H:10]([C:9]([NH:8][C@@H:7]([C:6]([NH:5][C@@H:4]([C:3]([NH2:61])=[O:2])[CH3:59])=[O:58])[CH2:43][C:44]1[CH:49]=[CH:48][C:47]([O:50][CH2:51][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:46][CH:45]=1)=[O:42])[CH2:33][O:34][CH2:35][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:32])[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 54340573Nalpha-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-D-tyrosyl-D-alanine methyl ester

Product 1

HCID 53958670Nalpha-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-D-tyrosyl-D-alaninamide

Procedure

The methyl ester of Example 10, 300 mg., is dissolved in 100 ml. of methanol saturated with ammonia and kept for 4 days at room temperature. The crude product is chromatographed on silica gel in chloroform-methanol-water (60:30:5) to yield 0.14 g.; m.p. 180°-185° C.

Workup

  1. dissolution, is dissolved in 100 ml
  2. customThe crude product is chromatographed on silica gel in chloroform-methanol-water (60:30:5)
  3. customto yield 0.14 g

Sources & evidence

ORD record
ord-616a712368e2403da4f290160e8397c0
Source dataset
uspto-grants-1977_06
Patent number
US04031069

Reaction notes

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