Formic Acid → HCID 131727858, compound

HRID 1994428Notes

Reaction equation

HRID 1994428 reaction equation
C(OC(=O)[NH:10][CH:11]([C:25](=[O:50])[NH:26][CH:27]([C:36](=[O:49])[N:37]([CH2:41][CH:42](OCC)OCC)[CH2:38][CH2:39][F:40])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])(=[O:16])=[O:15])C1C=CC=CC=1.[CH:52]([OH:54])=[O:53]>>[CH2:28]([O:53][C:52](=[O:54])[NH:10][CH:11]1[C:25](=[O:50])[N:26]2[CH:27]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=3)[C:36](=[O:49])[N:37]([CH2:38][CH2:39][F:40])[CH2:41][CH:42]2[N:13]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])(=[O:15])=[O:16])[CH2:12]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 131727859HCID 131727859, compound

Product 1

HCID 131727858HCID 131727858, compound

Procedure

A solution of 3.13 g (3.96 mmol) of benzyl[1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)(2-fluoroethyl)carbamoyl]ethylcarbamoyl}-2-(2,4-dichlorobenzenesulfonylamino)ethyl]carbamate in 20 ml of formic acid was heated to 60° C. and stirred for 6 hours. The reaction mixture was concentrated in vacuo, diluted with EtOAc and washed with 1N NaHCO3 solution and brine. The organic phase was isolated, dried (MgSO4) and concentrated in vacuo. This crude substance was subjected to a flash chromatography on 120 g of SiO2 (elution with EtOAc/heptane, gradient 50-100%). 350 mg of the substance benzyl[6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-(2-fluoroethyl)-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate were obtained. Further elution of the column provided 980 mg of the compound corresponding to the benzyl[6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-8-(2-hydroxyethyl)-4,7-dioxooctahydropyrazino[1,2-a]pyrimidin-3-yl]carbamate byproduct. The monoisotopic MW expected in the LC/MS=694 and the measured value of (M+H)=695 agree with the structure.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washwashed with 1N NaHCO3 solution and brine
  4. customThe organic phase was isolated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7264cccf2b3145c8a72376a13d6dd130
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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