Oxalyl chloride → HCID 178484082, compound

HRID 1063635Notes

Reaction equation

HRID 1063635 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]([N:9]([CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([OH:20])=O)[CH2:14][CH2:13]2)[CH3:10])=[O:8])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:29][NH:30][CH2:31][CH2:32][CH2:33][OH:34]>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7](=[O:8])[N:9]([CH2:11][C@H:12]2[CH2:13][CH2:14][C@H:15]([C:18](=[O:20])[N:30]([CH2:31][CH2:32][CH2:33][OH:34])[CH3:29])[CH2:16][CH2:17]2)[CH3:10])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 101489863-(Methylamino)-1-propanolHCID 178484085HCID 178484085, compound

Product 1

HCID 178484082HCID 178484082, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.09 g (0.276 mmol) of trans-4-{[(4-chloro-phenoxycarbonyl)-methyl-amino]-methyl}-cyclohexanecarboxylic acid in 2.5 mL of CH2Cl2 was treated at RT with 1 drop of DMF. 0.026 mL (0.304 mmol, 1.1 eq) of oxalyl chloride was added within 5 min and stirring was continued for 90 min. The solution was evaporated, redissolved in 2.5 mL of CH2Cl2 and added to a solution of 0.197 mL (2.21 mmol, 7.2 eq) of 3-(methylamino)-1-propanol [Powell et al., Synthesis (1986), (4), 338-40]at 0° C. The reaction was kept over night at RT, then partitioned between Et2O (×3)/aqueous saturated NaHCO3. The organic phases were washed once with aqueous 10% NaCl, dried over Na2SO4 and evaporated. Purification by flash-chromatography on 5 g silica gel (EtOAc:CH2Cl2 1:9 to 9:1) gave 0.064 g (58%) of pure trans-{4-[(3-hydroxy-propyl)-methyl-carbamoyl]-cyclohexylmethyl}-methyl-carbamic acid 4-chloro-phenyl ester, MS: 397 (MH+, 1Cl).

Workup

  1. customThe solution was evaporated
  2. dissolutionredissolved in 2.5 mL of CH2Cl2
  3. customPowell et al., Synthesis (1986), (4), 338-40]at 0° C
  4. waitThe reaction was kept over night at RT
  5. custompartitioned between Et2O (×3)/aqueous saturated NaHCO3
  6. washThe organic phases were washed once with aqueous 10% NaCl
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customPurification by flash-chromatography on 5 g silica gel (EtOAc:CH2Cl2 1:9 to 9:1)

Sources & evidence

ORD record
ord-4b6685a0ef45473eb3c012a9a4759642
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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