Boc-Tyr-ONB → BOC-Tyr-(D)-Met(O2)-Gly-Phe-NHNH-COCH3

HRID 1277409Notes

Reaction equation

HRID 1277409 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:9]([NH:11][CH2:12][C:13]([NH:15][C@H:16]([C:24]([NH:26][NH:27][C:28]([CH3:30])=[O:29])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])=[O:10])[CH2:3][CH2:4][S:5]([CH3:8])(=[O:7])=[O:6].[CH3:38][C:39]([O:42][C:43]([NH:45][C@H:46]([C:55]([O:57]CC1C=CC([N+]([O-])=O)=CC=1)=O)[CH2:47][C:48]1[CH:53]=[CH:52][C:51]([OH:54])=[CH:50][CH:49]=1)=[O:44])([CH3:41])[CH3:40]>>[NH:45]([C:43]([O:42][C:39]([CH3:38])([CH3:40])[CH3:41])=[O:44])[C@H:46]([C:55]([NH:1][C@@H:2]([C:9]([NH:11][CH2:12][C:13]([NH:15][C@H:16]([C:24]([NH:26][NH:27][C:28]([CH3:30])=[O:29])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])=[O:10])[CH2:3][CH2:4][S:5]([CH3:8])(=[O:7])=[O:6])=[O:57])[CH2:47][C:48]1[CH:49]=[CH:50][C:51]([OH:54])=[CH:52][CH:53]=1

Participants

3

Reactant 2

HCID 6995563Boc-Tyr-ONBHCID 12802564BOC-(D)-Met(O2)-Gly-Phe-NHNH-COCH3

Product 1

HCID 12802530BOC-Tyr-(D)-Met(O2)-Gly-Phe-NHNH-COCH3

Procedure

Using BOC-(D)-Met(O2)-Gly-Phe-NHNH-COCH3 (0.52 g) and BOC-Tyr-ONB(0.46 g), the desired compound is obtained in a similar manner to (V) of Example 26. m.p. 176°-177° C. [α]D23 -2.9°(c=0.24, DMF), Rf1 =0.23.

Sources & evidence

ORD record
ord-5dac65fac3984385b1850848f98a320d
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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