Methyl chloroformate → HCID 10150484, compound

HRID 1816439Notes

Reaction equation

HRID 1816439 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[O:6]=[S:7]1(=[O:32])[CH:12]=[CH:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25]C(=O)C(F)F)[O:21][C:20]3=[O:31])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1>N1C=CC=CC=1.ClCCl>[O:32]=[S:7]1(=[O:6])[CH:8]=[CH:9][CH:10]([C:13]2[CH:14]=[CH:15][C:16]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:2](=[O:3])[O:4][CH3:5])[O:21][C:20]3=[O:31])=[CH:17][CH:18]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 10216150HCID 10216150, compound

Product 1

HCID 10150484HCID 10150484, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl chloroformate (0.072 mL, 0.925 mmol) is added dropwise at 0° C. to to the crude amine hydrochloride prepared in Step 1 of Example 15 (0.316 g, 0.881 mmol) in a mixture of pyridine (4 mL) and dichloromethane (4 mL). The mixture is allowed to warm to room temperature, stirred for 1 hour, and then evaporated to dryness. The residue is purified by PTLC (10% methanol/dichloromethane) to give white solid (0.26 g, 78%). M.p. 196-7° C.

Workup

  1. customevaporated to dryness
  2. customThe residue is purified by PTLC (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-ab109af36d854e58b7c6629c2676f3f0
Source dataset
uspto-grants-2005_04
Patent number
US06884813B2

Reaction notes

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