Formic Acid → Benzyl [6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate

HRID 1670500Notes

Reaction equation

HRID 1670500 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][CH2:13][CH:14]([NH:41]C(=O)OCC1C=CC=CC=1)[C:15](=[O:40])[NH:16][CH:17]([C:26](=[O:39])[N:27]([CH2:31][CH:32](OCC)OCC)[CH:28]([CH3:30])[CH3:29])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)(=[O:11])=[O:10].[CH:52]([OH:54])=[O:53]>>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][CH:17]2[N:16]3[C:15](=[O:40])[CH:14]([NH:41][C:52](=[O:54])[O:53][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:13][N:12]([S:9]([C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])(=[O:11])=[O:10])[CH:32]3[CH2:31][N:27]([CH:28]([CH3:29])[CH3:30])[C:26]2=[O:39])=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 86761389Benzyl (2-(2,4-dichlorobenzenesulfonylamino)-1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate

Product 1

HCID 86761388Benzyl [6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-isopropyl-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate

Procedure

A solution of 218 mg of benzyl (2-(2,4-dichlorobenzenesulfonylamino)-1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}ethyl)carbamate in 3 ml of formic acid is stirred at room temperature for 12 h and then at 55° C. for 5 h. The reaction solution is concentrated under reduced pressure, and the residue is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90). The desired product is obtained with MW=692.10 (calculated monoisotopic); measured value (M+H)+: 693.05.

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. customthe residue is separated by HPLC (Knauer Eurospher-100-10-C18, water (0.1% trifluoroacetic acid)/acetonitrile (0.1% trifluoroacetic acid)=80/20→10/90)

Sources & evidence

ORD record
ord-8112e5e4536c4471b6bd2f11e82b5603
Source dataset
uspto-grants-2011_08
Patent number
US07994168B2

Reaction notes

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