Ethylmorpholine → HCID 178484646, compound

HRID 1063650Notes

Reaction equation

HRID 1063650 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:21])[CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][C:18]([OH:20])=O)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][NH:23][CH2:24][CH2:25][OH:26].C(N1CCOCC1)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CCOCC.Cl>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][C@H:11]1[CH2:12][CH2:13][C@H:14]([CH2:17][C:18](=[O:20])[N:23]([CH2:24][CH2:25][OH:26])[CH3:22])[CH2:15][CH2:16]1)[CH3:21])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 80162-(Methylamino)ethanolHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178483642HCID 178483642, compound

Product 1

HCID 178484646HCID 178484646, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 200 mg (0.67 mmol) of trans-{4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexyl}-acetic acid and 0.065 mL (0.8 mmol, 1.2 eq) of 2-(methylamino)-ethanol were added 0.4 mL (3.3 mmol, 5 eq) of 4-ethylmorpholine and 0.31 g (0.7 mmol, 1.05 eq) of BOP at RT. The solution was stirred at RT for 3 h, diluted with ether and 1M HCl was added. The phases were separated and the organic phases were washed with water and brine and dried over magnesium sulfate. Evaporation yielded 234 mg (quantitative) of crude trans [2-(4-{[(2-hydroxy-ethyl)-methyl-carbamoyl]-methyl}-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester as colorless oil, MS: 357 (MH+).

Workup

  1. additionwas added
  2. customThe phases were separated
  3. washthe organic phases were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation

Sources & evidence

ORD record
ord-a494250514804024845024f33e62e5ec
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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