Methyl chloroformate → HCID 86726387, compound

HRID 629776Notes

Reaction equation

HRID 629776 reaction equation
[NH2:1][C@@H:2]([C@@H:38]([C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[C:47]([Cl:53])[CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:3]([NH:5][C:6]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:7]=1[CH2:8][CH2:9][C@H:10]1[O:15][CH2:14][C@@H:13]([CH2:16][O:17][C:18](=[O:25])[NH:19][CH2:20][C:21]([F:24])([F:23])[F:22])[N:12]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:11]1)=[O:4].C(N(CC)CC)C.Cl[C:62]([O:64][CH3:65])=[O:63]>ClCCl>[Cl:53][C:47]1[CH:46]=[C:45]([C@@H:38]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C@H:2]([NH:1][C:62]([O:64][CH3:65])=[O:63])[C:3]([NH:5][C:6]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:7]=2[CH2:8][CH2:9][C@H:10]2[O:15][CH2:14][C@@H:13]([CH2:16][O:17][C:18](=[O:25])[NH:19][CH2:20][C:21]([F:24])([F:23])[F:22])[N:12]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[CH2:11]2)=[O:4])[CH:50]=[CH:49][C:48]=1[O:51][CH3:52]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 86726386HCID 86726386, compound

Product 1

HCID 86726387HCID 86726387, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of the product from step 3 (80 mg, 0.1 mmol) in dichloromethane (2 mL) was added triethylamine (0.02 mL, 0.16 mmol) and methyl chloroformate (0.01 mL, 0.12 mmol). The mixture was stirred at ambient temperature for 6 h, then diluted with dichloromethane (10 mL) and washed with aqueous NaHCO3 and brine. The organic phase was dried (MgSO4), filtered, and the solvents were removed in vacuo. The residue was chromatographed on a 12 g SiO2 column using a gradient elution of 0-100% EtOc in hexanes. Fractions containing product were combined and the solvents were removed in vacuo to give the title compound as a gum. (M+H)+=825.

Workup

  1. washwashed with aqueous NaHCO3 and brine
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvents were removed in vacuo
  5. customThe residue was chromatographed on a 12 g SiO2 column
  6. washa gradient elution of 0-100% EtOc in hexanes
  7. additionFractions containing product
  8. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-a8c2be5aff65400f84b5ccdf10bfad1d
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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