Methyl chloroformate → HCID 57463856, compound

HRID 1292663Notes

Reaction equation

HRID 1292663 reaction equation
[C:1]1([CH2:11][NH:12][CH2:13][C@@H:14]([NH:19][C:20](=[O:36])[CH2:21][C:22]2[N:26]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=3)[CH:25]=[N:24][CH:23]=2)[C@@H:15]([CH3:18])[CH2:16][CH3:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:45]([O:47][CH3:48])=[O:46]>ClCl>[CH3:48][O:47][C:45]([N:12]([CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH2:13][C@@H:14]([NH:19][C:20](=[O:36])[CH2:21][C:22]1[N:26]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=2)[CH:25]=[N:24][CH:23]=1)[C@@H:15]([CH3:18])[CH2:16][CH3:17])=[O:46]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 57463855HCID 57463855, compound

Product 1

HCID 57463856HCID 57463856, compound

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent2×

Procedure

To a solution of the product of Example 2 (40 mg, 0.083 mmol) in CH2 Cl2 (1 ml) and triethylamine (24 μl, 0.17 mmol) at 0° C. was added methyl chloroformate (39 μl of a 2.1M solution in CH2 Cl2, 0.082 mmol). The reaction was stirred at room temperature for 3 hr, the solvent evaporated in vacuo and the residue purified by preparative HPLC (C-18; 95:5 to 5:95 water:CH3CN containing 0.1% trifluoroacetic acid; gradient elution). Lyophilisation of the collected fractions afforded the title compound as a white solid.

Workup

  1. customthe solvent evaporated in vacuo
  2. customthe residue purified by preparative HPLC (C-18; 95:5 to 5:95 water:CH3CN containing 0.1% trifluoroacetic acid; gradient elution)

Sources & evidence

ORD record
ord-e1a7f08350154b0baf6ebbb29bf7ab04
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

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