N-(tert-Butoxycarbonyl)-L-tyrosyl-D-methionylglycine → BOC-(D)-Phe-Gly-Phe-NHNH-COCH3

HRID 1277402Notes

Reaction equation

HRID 1277402 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][NH:17][C:18]([CH3:20])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[NH:21]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C@H:22]([C:31](N[C@@H](C(NCC(O)=O)=O)CCSC)=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1>CN(C=O)C>[NH:21]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C@@H:22]([C:31]([NH:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][NH:17][C:18]([CH3:20])=[O:19])=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4])=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 12919645N-(tert-Butoxycarbonyl)-L-tyrosyl-D-methionylglycineHCID 131712285H-Gly-Phe-NHNH-COCH3

Product 1

HCID 12802554BOC-(D)-Phe-Gly-Phe-NHNH-COCH3

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using H-Gly-Phe-NHNH-COCH3 (0.44 g) and BOC-(D)-Phe-ONB (0.68 g), the desired compound (0.68 g) is obtained in a similar manner to (III) of Example 45, m.p. 208°-209° C., [α]D23 +3.3°(c=0.45, DMF), Rf1 =0.51.

Sources & evidence

ORD record
ord-36edcd170ca74d10bb2b513f51f15e19
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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