Oxalyl chloride → 1-(Chlorocarbonylmethyl)-N4-(benzyloxycarbonyl)cytosine

HRID 355492Notes

Reaction equation

HRID 355492 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].C(C[N:11]1[CH:28]=[CH:27][C:15]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[N:14][C:12]1=[O:13])(O)=O>ClCCl>[Cl:4][C:2]([CH2:1][N:11]1[CH:28]=[CH:27][C:15]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[N:14][C:12]1=[O:13])=[O:3]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 7254702-(4-(((Benzyloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid

Product 1

HCID 235111841-(Chlorocarbonylmethyl)-N4-(benzyloxycarbonyl)cytosine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (6.3 g, 50 mmol) is added dropwise over 5 minutes to a solution of 1-(carboxymethyl)-N4-(benzyloxycarbonyl)cytosine (15.3 g, 50 mmol) dissolved in dichloromethane (200 mL). The reaction is stirred until gas evolution has ceased and then for an additional 2 hours. The reaction mixture is evaporated to an oil.

Workup

  1. customThe reaction mixture is evaporated to an oil

Sources & evidence

ORD record
ord-5b1e0d6e8efb4e7d9cc0eb2ded986bcc
Source dataset
uspto-grants-1998_11
Patent number
US05831014

Reaction notes

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