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

HRID 1277401Notes

Reaction equation

HRID 1277401 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].N([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C@H](C(N[C@@H](C(NCC(O)=O)=O)CCSC)=O)CC1C=CC(O)=CC=1>>[NH:1]([C:46]([O:48][C:49]([CH3:50])([CH3:52])[CH3:51])=[O:47])[C@@H: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])[CH2:7][CH2:6][C:14](=[O:15])[NH2:16]

Participants

3

Reactant 2

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

Product 1

HCID 131712287BOC-(D)-Gln-Phe-NHNH-COCH3

Procedure

Using BOC-(D)-Gln-ONP(0.96 g) and H-Gly-Phe-NHNH-COCH3 (0.72 g), the desired compound (0.95 g) is obtained in a similar manner to (III) of Example 45. m.p. 198°-199° C., [α]D23 -0.8° (C=0.50, DMF), Rf1 =0.19.

Sources & evidence

ORD record
ord-f9e0ab7424b84c7a823ee34f004acbd9
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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