Acetate-hydrochloric acid → HCID 131719313, compound

HRID 1488444Notes

Reaction equation

HRID 1488444 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([N:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([OH:16])=[O:15])=[O:11])[CH2:3][S:4][CH2:5][NH:6][C:7]([CH3:9])=[O:8].[ClH:27].CC(O)=O>CN(C=O)C>[NH2:1][C@H:2]([C:10]([N:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([OH:16])=[O:15])=[O:11])[CH2:3][S:4][CH2:5][NH:6][C:7]([CH3:9])=[O:8].[ClH:27]

Participants

4

Reactant 2

HCID 22641269Acetate-hydrochloric acidHCID 131719316HCID 131719316, compound

Product 1

HCID 131719313HCID 131719313, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

BocCys(Acm)ONp is prepared from BocCys(Acm)OH (Novabiochem, Laufelingen, CH) and p-nitrophenol by reaction with N,N'-dicyclohexylcarbodiimide (DCC) in ethyl acetate and used without purification for the preparation of Boc-Cys(Acm)-Pro-OH (XII) by reacting it with H-Pro-OH in DMF/etyl acetate/HCl at 0° C. while keeping pH neutral by addition of Et3N. Yield 81%. Purity >95% (TLC). Boc-Asn-Cys(Acm)-Pro-OH (XIII) is obtained by deblocking XII in HCl/HOAc att room temperature, dissolving the thus obtained raw H-Cys(Acm)-Pro-OH·HCl in DMF and neutralizing it with Et3N, and adding Boc-Asn-ONp (Novabiochem, Laufelingen, CH) at -5° C. while keeping pH neutral. XIII is isolated in 81% yield. [α]D20 =-77.1° (1 g/100 ml DMF). The tetrapeptide derivative X is prepared from XIII and Boc-Gln-ONp (Novabiochem, Laufelingen, CH) in a way corresponding to the preparation of XIII from XII and Boc-Asn-ONp. Yield 78.5%; [α]D20 =-89.7° (1 g/100 ml H2O).

Workup

  1. customatt room temperature
  2. dissolutiondissolving the

Sources & evidence

ORD record
ord-445803a390ed46568c76e4d39079a6ee
Source dataset
uspto-grants-1997_10
Patent number
US05674850

Reaction notes

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