Methyl chloroformate → HCID 11181605, compound

HRID 1174390Notes

Reaction equation

HRID 1174390 reaction equation
[CH2:1]([C@H:8]([NH:39][C:40](=[O:47])[C@H:41]([CH2:43][CH:44]([CH3:46])[CH3:45])[NH2:42])[C@@H:9]([OH:38])[CH2:10][C@@H:11]([NH:25][C:26](=[O:37])[C@H:27]([C:33]([CH3:36])([CH3:35])[CH3:34])[NH:28][C:29]([O:31][CH3:32])=[O:30])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:49]([O:51][CH3:52])=[O:50].C(N(CC)CC)C>ClCCl>[CH3:52][O:51][C:49](=[O:50])[NH:42][C@@H:41]([CH2:43][CH:44]([CH3:45])[CH3:46])[C:40](=[O:47])[NH:39][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]([OH:38])[CH2:10][C@H:11]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:15][CH:14]=1)[NH:25][C:26](=[O:37])[C@H:27]([C:33]([CH3:36])([CH3:35])[CH3:34])[NH:28][C:29](=[O:30])[O:31][CH3:32]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 67406902HCID 67406902, compound

Product 1

HCID 11181605HCID 11181605, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 167B (11.2 mg, 0.017 mmol) in dichloromethane (0.25 mL) was treated with methyl chloroformate (2 μL, 0.026 mmol), and triethylamine (4.8 μL, 0.034 mmol) at 25° C. for 1 h. The solvents were evaporated, and the crude residue was purified by silica gel chromatography eluting with a gradient of dichloromethane, 100% ethyl acetate, and 95% ethyl acetate/7% methanol to give the title compound (7 mg, 57%). 1H NMR (300 MHz, CDCl3)δ ppm 0.87-0.84(s, 15H), 1.34-1.29(m, 2H), 1.65-1.51(m, 3H), 2.67-2.60(m, 2H), 2.86-2.83(d, J=7.72 Hz, 2H), 2.95-2.87(m, 1H), 3.52(s, 3H), 3.65(s, 3H), 3.78-3.73(m, 1H), 3.81(s, 1H), 4.08-4.03(m, 1H), 4.24-4.19(m, 1H), 4.33(m, 1H), 7.17-7.12(m, 1H), 7.26-7.20(m, H), 7.29-7.26(d, J=8.46 Hz, 2H), 7.35-7.30(m, 1H), 7.81-7.77(m, 3H), 7.90-7.84(m, 1H).

Workup

  1. customThe solvents were evaporated
  2. customthe crude residue was purified by silica gel chromatography
  3. washeluting with a gradient of dichloromethane, 100% ethyl acetate, and 95% ethyl acetate/7% methanol

Sources & evidence

ORD record
ord-5e28d12b43b546048924383f6c4e6bfd
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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