Boc-Tyr-ONB → BOC-Tyr-(D)-Met(O)-Gly-MePhe-NHNH-CO-CH3

HRID 1277411Notes

Reaction equation

HRID 1277411 reaction equation
N(C(OC(C)(C)C)=O)[C@@H:2]([C:8]([NH:10][CH2:11][C:12]([N:14]([CH3:30])[C@H:15]([C:23]([NH:25][NH:26][C:27]([CH3:29])=[O:28])=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])=[O:9])[CH2:3][CH2:4][S:5]([CH3:7])=[O:6].CC(OC(N[C@H](C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)CC1C=CC(O)=CC=1)=O)(C)C.[NH:68]([C:93]([O:95][C:96]([CH3:99])([CH3:98])[CH3:97])=[O:94])[C@H:69]([C:78]([NH:80][C@@H](C(NCC(O)=O)=O)CCSC)=[O:79])[CH2:70][C:71]1[CH:76]=[CH:75][C:74]([OH:77])=[CH:73][CH:72]=1>CN(C=O)C>[NH:68]([C:93]([O:95][C:96]([CH3:99])([CH3:98])[CH3:97])=[O:94])[C@H:69]([C:78]([NH:80][C@@H:2]([C:8]([NH:10][CH2:11][C:12]([N:14]([CH3:30])[C@H:15]([C:23]([NH:25][NH:26][C:27]([CH3:29])=[O:28])=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])=[O:9])[CH2:3][CH2:4][S:5]([CH3:7])=[O:6])=[O:79])[CH2:70][C:71]1[CH:72]=[CH:73][C:74]([OH:77])=[CH:75][CH:76]=1

Participants

5

Reactant 3

HCID 6995563Boc-Tyr-ONBHCID 12919645N-(tert-Butoxycarbonyl)-L-tyrosyl-D-methionylglycineHCID 12919690BOC-(D)-Met(O)-Gly-MePhe-NHNH-CO-CH3

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 0.54 g of BOC-(D)-Met(O)-Gly-MePhe-NHNH-CO-CH3 and 0.46 g of BOC-Tyr-ONB in a similar manner to (III) of Example 36 is obtained (0.46 g) of the desired product, m.p. 141°-142° C., [α]D22 -25.4° (c=0.48, DMF), Rf1 =0.22.

Sources & evidence

ORD record
ord-03bb0c45e3d14dc8a376fd506a07fdc7
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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