Methanol → BOC-Tyr-(D)-Met(O)-Gly-OH

HRID 1277412Notes

Reaction equation

HRID 1277412 reaction equation
[NH:1]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@H:2]([C:11]([NH:13][C@@H:14]([C:20]([NH:22][CH2:23][C:24]([N:26]([CH3:42])[C@H:27]([C:35]([NH:37][NH:38][C:39]([CH3:41])=[O:40])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])=[O:21])[CH2:15][CH2:16][S:17]([CH3:19])=[O:18])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C[OH:51]>>[NH:1]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[C@H:2]([C:11]([NH:13][C@@H:14]([C:20]([NH:22][CH2:23][C:24]([OH:25])=[O:51])=[O:21])[CH2:15][CH2:16][S:17]([CH3:19])=[O:18])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1.[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:20]([NH:22][CH2:23][C:24]([N:26]([CH3:42])[C@H:27]([C:35]([NH:37][NH:38][C:39]([CH3:41])=[O:40])=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:25])=[O:21])[CH2:15][CH2:16][S:17]([CH3:19])=[O:18])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 12919692BOC-Tyr-(D)-Met(O)-Gly-MePhe-NHNH-CO-CH3

Product 2

HCID 12919648BOC-Tyr-(D)-Met(O)-Gly-OHHCID 12919694H-Tyr-(D)-Met(O)-Gly-MePhe-NHNH-CO-CH3

Procedure

Using 0.35 g of BOC-Tyr-(D)-Met(O)-Gly-MePhe-NHNH-CO-CH3, in a similarmanner to (IV) of Example 36 is obtained 0.19 g of the desired product, [α]D22 0° (c=0.25, MeOH), Rf2 =0.16, amino acid analysis: Gly 1.00, Met 1.00, Tyr 1.20.

Sources & evidence

ORD record
ord-fc0a07ee532c4de3a11d89be3b047254
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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