Boc-Tyr-ONB → BOC-Tyr-(D)-Lys(Cl-Z)-Gly-Phe-NHNH-COCH3

HRID 1277404Notes

Reaction equation

HRID 1277404 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:19]([NH:21][CH2:22][C:23]([NH:25][C@H:26]([C:34]([NH:36][NH:37][C:38]([CH3:40])=[O:39])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[Cl:14])=[O:9].[CH3:48][C:49]([O:52][C:53]([NH:55][C@H:56]([C:65]([O:67]CC1C=CC([N+]([O-])=O)=CC=1)=O)[CH2:57][C:58]1[CH:63]=[CH:62][C:61]([OH:64])=[CH:60][CH:59]=1)=[O:54])([CH3:51])[CH3:50]>>[NH:55]([C:53]([O:52][C:49]([CH3:48])([CH3:50])[CH3:51])=[O:54])[C@H:56]([C:65]([NH:1][C@@H:2]([C:19]([NH:21][CH2:22][C:23]([NH:25][C@H:26]([C:34]([NH:36][NH:37][C:38]([CH3:40])=[O:39])=[O:35])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:24])=[O:20])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[Cl:14])=[O:9])=[O:67])[CH2:57][C:58]1[CH:59]=[CH:60][C:61]([OH:64])=[CH:62][CH:63]=1

Participants

3

Reactant 2

HCID 6995563Boc-Tyr-ONBHCID 131712289BOC-(D)-Lys(Cl-Z)-Gly-Phe-NHNH-COCH3

Product 1

HCID 131712288BOC-Tyr-(D)-Lys(Cl-Z)-Gly-Phe-NHNH-COCH3Yield 81.7%

Procedure

Using BOC-(D)-Lys(Cl-Z)-Gly-Phe-NHNH-COCH3 (0.70 g) and BOC-Tyr-ONB (0.50 g), the desired compound (0.71 g) is obtained in a similar manner to(V) of Example 26. m.p. 196°-198° C., [α]D23 -2.0°(c=0.47, DMF), Rf1 =0.46

Sources & evidence

ORD record
ord-cee5a002558f42d98bf33ae04a9320e0
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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