Stearyl Alcohol → HCID 13190109, compound

HRID 1164381Notes

Reaction equation

HRID 1164381 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([NH:15][C@@H:16]([C:22](=[O:24])[NH2:23])[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC2N=NN(OS(C3C=CC(Cl)=CC=3)(=O)=O)C=2C=1.[CH2:46](O)[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([NH:15][C@@H:16]([C:22](=[O:24])[NH2:23])[CH2:17][CH2:18][C:19]([O:21][CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH3:46])=[O:20])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 8221Stearyl AlcoholHCID 122228411-(p-Chlorobenzenesulfonyloxy)-6-chloro-1,2,3-benzotriazoleHCID 13190105HCID 13190105, compound

Product 1

HCID 13190109HCID 13190109, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butyloxycarbonyl-L-valyl-D-isoglutamine (1.73 g, 5 mmol) and 6-chloro-1-p-chlorobenzenesulfonyloxybenzotriazole (2.06 g, 6 mmol) were reacted in DMF (5 ml) in the presence of TEA (0.84 ml) in a similar manner to that in Example 6 (II). Then stearyl alcohol (4.05 g, 15 mmol) and TEA (0.7 ml) were added and the mixture was reacted at room temperature for 20 hours. The usual work-up as described in Example 6 (II) gave stearyl t-butyloxycarbonyl-L-valyl-D-isoglutaminate (1.10 g). m.p. 88°-89° C. [α]D23 +4.0° (C 0.5, DMF). Rf2 =0.68, Rf3 =0.34

Workup

  1. customthe mixture was reacted at room temperature for 20 hours

Sources & evidence

ORD record
ord-7063b7bf5c1e44baa76173c0bca10fa4
Source dataset
uspto-grants-1983_01
Patent number
US04369178

Reaction notes

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