Methyl chloroformate → HCID 178498181, compound

HRID 1053830Notes

Reaction equation

HRID 1053830 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH2:9][C@@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([N:18]2[CH2:22][C@@H:21]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH2:20][C@H:19]2[C:29]([NH:31][C:32]2[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=2)=[O:30])=[O:17])[CH2:12][CH2:11]1)=[O:7])([CH3:4])[CH3:3].C(N(CC)CC)C.Cl[C:50]([O:52][CH3:53])=[O:51]>ClCCl>[CH3:39][O:38][C:36]([C:35]1[CH:34]=[CH:33][C:32]([NH:31][C:29]([C@H:19]2[N:18]([C:16]([C@H:13]3[CH2:14][CH2:15][C@@H:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:11][CH2:12]3)=[O:17])[CH2:22][C@@H:21]([N:23]3[CH2:28][CH2:27][N:26]([C:50]([O:52][CH3:53])=[O:51])[CH2:25][CH2:24]3)[CH2:20]2)=[O:30])=[CH:41][CH:40]=1)=[O:37]

Participants

5

Reactant 3

HCID 6586Methyl chloroformate2×HCID 8471TriethylamineHCID 178498179HCID 178498179, compound

Product 1

HCID 178498181HCID 178498181, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the compound prepared in Example 50 (150 mg) in dichloromethane (3 mL) was added triethylamine (0.3 mL) and methyl chloroformate (22 μL). The mixture was stirred at room temperature overnight. Further methyl chloroformate (11 μL) was added and the reaction stirred at room temperature for an additional 4 days. The reaction mixture was partitioned between dichloromethane (20 mL) and brine (20 mL), the organic layer separated, dried and concentrated. The residue was purified by column chromatography (silica gel, ethyl acetate) to give the title compound (119 mg) as a white solid.

Workup

  1. stirringthe reaction stirred at room temperature for an additional 4 days
  2. customThe reaction mixture was partitioned between dichloromethane (20 mL) and brine (20 mL)
  3. customthe organic layer separated
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-d78c6b0595974c66be61a811f6ac5995
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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