Methanol → HCID 54384546, compound

HRID 259005Notes

Reaction equation

HRID 259005 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([NH:22][C@H:23]([C:39]([NH:41][C@H:42]([C:52]([NH:54][C@@H:55]([C:57]([OH:59])=[O:58])[CH3:56])=[O:53])[CH2:43][O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:40])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:27][CH:26]=1)=[O:21])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:60]O>C(N(CC)CC)C>[CH3:60][O:58][C:57](=[O:59])[C@@H:55]([CH3:56])[NH:54][C:52](=[O:53])[C@H:42]([CH2:43][O:44][CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[NH:41][C:39](=[O:40])[C@H:23]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:27][CH:26]=1)[NH:22][C:20](=[O:21])[C@H:9]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

4

Reactant 2

HCID 887MethanolHCID 53666591HCID 53666591, compound

Product 1

HCID 54384546HCID 54384546, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Nα-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-tyrosyl-O-benzyl-L-seryl-D-alanine resin, 7.1 g., prepared in Example 1 is mixed with methanol, 600 ml., and triethylamine, 60 ml., at room temperature for 2 days. After filtration and evaporation, the crude product, 2.7 g., is chromatographed on silica gel with chloroform-methanol-water (60:30:5) to yield 1.9 g., m.p. 178°-182° C.

Workup

  1. custom, prepared in Example 1
  2. filtrationAfter filtration and evaporation
  3. custom, is chromatographed on silica gel with chloroform-methanol-water (60:30:5)
  4. customto yield 1.9 g

Sources & evidence

ORD record
ord-f5796053dd794918a21d7ad0e5929484
Source dataset
uspto-grants-1977_07
Patent number
US04035348

Reaction notes

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