Dimethylformamide → HCID 18609891, compound

HRID 838875Notes

Reaction equation

HRID 838875 reaction equation
[C:1]([NH:20][C@H](C(O)=O)CSC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([C:14]1[CH:19]=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O[N:47]1[C:51]2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.N1([O:80]C(=O)[C@H](CSC(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)NC(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2N=N1.C([N:127]1[CH2:132][CH2:131]OCC1)C.[CH3:133][N:134](C)[CH:135]=[O:136]>>[NH2:20][C@H:1]([C:135]([NH:134][CH2:133][C:51]([NH2:47])=[O:80])=[O:136])[CH2:14][CH2:19][CH2:131][CH2:132][NH2:127]

Participants

7

Reactant 6

HCID 6228Dimethylformamide2×HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 14081820HCID 14081820, compound2×HCID 86735737HCID 86735737, compound

Product 1

HCID 18609891HCID 18609891, compound

Procedure

In the next step of the process, N,S-ditrityl-cysteine is converted to its corresponding activated ester, preferably the 1-benzotriazolyl ester, by reacting N,S-ditrityl-cysteine with 1.0 to 1.3 molar equivalents of 1-hydroxybenzotriazole and dicyclohexylcarbodiimide in an inert organic solvent, i.e. dimethylformamide, at -10° to 10° C for 1 to 3 hours and at 20° to 30° C for an additional hour. The latter mixture containing N,S-ditrityl-cysteine 1-benzotriazolyl ester is cooled to -10° to 5° C and a solution of an equimolar amount of H--Pro--Lys(Boc)--Gly--NH2 and a sufficient amount of an organic acceptor, preferably N-ethylmorpholine, in an inert organic solvent, i.e. dimethylformamide, is added. The mixture is stirred at 20° to 30° C for 20 to 30 hours to obtain N,S-ditrityl-cysteinyl-prolyl-)Nε -t-butoxycarbonyl)lysyl-glycinamide (Trt--Cys(Trt)--Pro--Lys(Boc)--Gly--NH2), tetrapeptide fragment 9-12.

Workup

  1. waitat 20° to 30° C for an additional hour
  2. temperatureis cooled to -10° to 5° C

Sources & evidence

ORD record
ord-eeb6d19319a9480f8f38f408da22730a
Source dataset
uspto-grants-1978_06
Patent number
US04093610

Reaction notes

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