1-Hydroxybenzotriazole → HCID 131711962, compound

HRID 1732521Notes

Reaction equation

HRID 1732521 reaction equation
C(OC([NH:11][C@H:12]([C:16]([NH:18][C@H:19]([C:32]([NH2:34])=[O:33])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:17])[CH:13]([CH3:15])[CH3:14])=O)C1C=CC=CC=1.[CH3:35][C@H:36]([NH:49][C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[C:37]([O:39]C1C=CC([N+]([O-])=O)=CC=1)=O.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:53]([O:52][C:50]([NH:49][C@H:36]([C:37]([NH:11][C@H:12]([C:16]([NH:18][C@H:19]([C:32]([NH2:34])=[O:33])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])=[O:17])[CH:13]([CH3:14])[CH3:15])=[O:39])[CH3:35])=[O:51])[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 70218781168-87-2HCID 131711963HCID 131711963, compound2×

Product 1

HCID 131711962HCID 131711962, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A sample of compound XV (4.3 g, 9 mmole) was hydrogenated as described in the previous paragraph and the partially deblocked peptide (RfC, 0.60) was acylated with Z-L-Ala-ONp (3.47 g, 10 mmole, Bachem) in the presence of DIEA (3.2 ml, 20 mmole) and HOBt (1.3 g, 9 mmole). The product isolated as described for XV weighed 4.2 g (85%) m.p. 214°-217° C., [α]D24 -9.5° (c 0.8, DMF); RfB, 0.48; RfI, 0.33.

Workup

  1. customThe product isolated

Sources & evidence

ORD record
ord-9200d613e04c4e0fb08f047a9838725f
Source dataset
uspto-grants-1980_12
Patent number
US04237046

Reaction notes

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