Diisopropylethylamine → HCID 178483909, compound

HRID 1063630Notes

Reaction equation

HRID 1063630 reaction equation
Cl.[OH:2][CH2:3][CH2:4][CH2:5][N:6]([CH3:20])[C:7](=[O:19])[CH2:8][CH2:9][O:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][CH3:18])[CH2:13][CH2:12]1.C(N(CC)C(C)C)(C)C.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=1)=[O:32].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([O:33][C:31](=[O:32])[N:17]([C@H:14]2[CH2:13][CH2:12][C@H:11]([O:10][CH2:9][CH2:8][C:7](=[O:19])[N:6]([CH2:5][CH2:4][CH2:3][OH:2])[CH3:20])[CH2:16][CH2:15]2)[CH3:18])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 516892Sodium BicarbonateHCID 178484856HCID 178484856, compound

Product 1

HCID 178483909HCID 178483909, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 158 mg (0.5 mmol) of trans-N-(3-hydroxy-propyl)-N-methyl-3-(4-methylamino-cyclohexyloxy)-propionamide-hydrochloride in 3 mL of CH2Cl2 were added 0.43 mL (2.6 mmol, 5 eq) of N,N-diisopropylethylamine followed by 0.08 mL (0.56 mmol, 1.1 eq) of 4-chlorophenyl chloroformate. The mixture was stirred at RT for 1 h, and the solution was added to a mixture of NaHCO3 solution and CH2Cl2. The phases were separated and the inorganic phase was extracted with CH2Cl2. The organic phase was washed with 1M KHSO4. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated. Column chromatography on silica gel with a gradient of CH2Cl2:MeOH 98:2 to 95:5 yielded 105 mg (48%) of trans-(4-{2-[(3-hydroxy-propyl)-methyl-carbamoyl]-ethoxy}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester as colorless oil, MS: 427 (MH+,1Cl).

Workup

  1. customThe phases were separated
  2. extractionthe inorganic phase was extracted with CH2Cl2
  3. washThe organic phase was washed with 1M KHSO4
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-8c60875eb0314b398e525b1050191b99
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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