Dicyclohexylcarbodiimide → l-tryptophyl-D-alanine

HRID 839002Notes

Reaction equation

HRID 839002 reaction equation
C(O[C:6]([NH:8][C@@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])(C)(C)C.C(OC([NH:21][C@H:22](C(O)=O)[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1)=O)(C)(C)C.C1(N=C=NC2CCCCC2)CCCCC1.C(OC(N[C@H](C(O)=O)COCC1C=CC=CC=1)=O)(C)(C)C.C(OC(N[C@H](C(O)=O)CC1C=CC(OCC2C=CC=CC=2)=CC=1)=O)(C)(C)C.C(N[C@H](C(O)=O)CC1N=CNC=1)C1C=CC=CC=1.[N+](C1C=CC(OC(=O)[C@H](CCC(=O)N)NC(OCC2C=CC=CC=2)=O)=CC=1)([O-])=O>CN(C)C=O>[NH2:21][C@H:22]([C:6]([NH:8][C@@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])[CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1

Participants

9

Reactant 7

HCID 10868Dicyclohexylcarbodiimide6×HCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 111333Z-Gln-ONpHCID 637606BOC-D-alanineHCID 178525810CID 70151722×

Product 1

HCID 61578895l-tryptophyl-D-alanine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Nα -Benzyloxycarbonyl-L-glutaminyl-L-prolyl-Nim -benzyl-L-histidyl-Nim -benzyl-L-histidyl-O-benzyl-L-tyrosyl-O-benzyl-L-seryl=l-tryptophyl-D-alanine resin is prepared by the General Procedure, given below, by successive coupling of 30 g. (0.0198 mol) of Nα -t-butoxycarbonyl-D-alanine resin with 1.) 9.1 g (0.03 mol) of Nα -t-butoxycarbonyl-L-tryptophan and 6.8 g. (0.03 mol) of dicyclohexylcarbodiimide, 2.) 9.0 g. (0.03 mol) of Nα -t-butoxycarbonyl-O-benzyl-L-serine and 6.8 g. (0.033 mol) of dicyclohexylcarbodiimide, 3.) 11.1 g. (0.03 mol) of Nα -t-butoxycarbonyl-O-benzyl-L-tyrosine and 6.8 g. (0.033 mol) of dicyclohexylcarbodiimide, 4.) 10.5 g. (0.03 mol) of Nα -t-butoxycarbonyl-Nim -benzyl-L-histidine and 6.8 g. (0.033 mol) of dicyclohexylcarbodiimide, 5.) 10.5 g. (0.03 mol) of Nα -t-butoxycarbonyl-Nim -benzyl-L-histidine and 6.8 g. (0.033 mol) of dicyclohexylcarbodiimide, 6.) using 2/3 of the resin obtained in Step 5 with 4.4 g. (0.02 mol) of Nα -t-butoxycarbonyl-L-proline and 4.6 g. (0.022 mol) of dicyclohexylcarbodiimide and 7.) using 1/2 of the resin obtained in Step 6 with 8 g. (0.02 mol) of Nα -benzyloxycarbonyl-L-glutamine p-nitrophenyl ester in dimethylformamide solution and the excess removed by drainage.

Sources & evidence

ORD record
ord-2111de5050434072bbcd0622412c80f6
Source dataset
uspto-grants-1978_06
Patent number
US04093611

Reaction notes

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