Acetate-hydrochloric acid → HCID 131719313, compound

HRID 1440656Notes

Reaction equation

HRID 1440656 reaction equation
N(C(OC(C)(C)C)=O)[C@H](C([NH:9][C@H:10]([C:18]([N:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([OH:24])=[O:23])=[O:19])[CH2:11][S:12][CH2:13][NH:14][C:15]([CH3:17])=[O:16])=O)CC(=O)N.N(C(OC(C)(C)C)=O)[C@H](C(N1CCC[C@H]1C(O)=O)=O)CSCNC(C)=O.[ClH:61].CC(O)=O>CN(C=O)C>[NH2:9][C@H:10]([C:18]([N:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([OH:24])=[O:23])=[O:19])[CH2:11][S:12][CH2:13][NH:14][C:15]([CH3:17])=[O:16].[ClH:61]

Participants

5

Reactant 3

HCID 22641269Acetate-hydrochloric acidHCID 131719315HCID 131719315, compoundHCID 131719316HCID 131719316, compound

Product 1

HCID 131719313HCID 131719313, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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-3b8b097fc209438fb8ee577fc92e0ed4
Source dataset
uspto-grants-1996_03
Patent number
US05500413

Reaction notes

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