Triethylamine → HCID 89825002, compound

HRID 2277102Notes

Reaction equation

HRID 2277102 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[CH2:16][NH:17][C:18]([C@@H:20]1[CH2:25][S:24][CH2:23][CH2:22][NH:21]1)=[O:19])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:34]([O:37][C@H:38]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:39](Cl)=[O:40])(=[O:36])[CH3:35]>C(Cl)Cl>[C:34]([O:37][C@H:38]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:39]([N:21]1[CH2:22][CH2:23][S:24][CH2:25][C@H:20]1[C:18](=[O:19])[NH:17][CH2:16][C:10]1[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=1[CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:26])=[O:40])(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 89824898HCID 89824898, compoundHCID 89835598HCID 89835598, compound

Product 1

HCID 89825002HCID 89825002, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-tert-Butyl-4-chloro-2-{(thiomorpholine-3-carboxamido)-methyl}-benzyl-carbamate (0.56 g, 1.40 mmol) in CH2Cl2 (25 mL) was added triethyl amine (0.59 mL, 4.2 mmol) and solution of (2R)-1-chloro-3,3-dimethyl-1-oxobutan-2-yl acetate (0.496 g, 2.8 mmol) in CH2Cl2 (5 mL) dropwise at −10° C. and the resulting mixture was allowed to warm up to room temperature over 1 h. The reaction mixture was quenched with water (50 mL) and extracted with EtOAc (3×25 mL). The combined organic layers were washed with brine solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase combiflash column chromatography (C18; eluent: 10-100% acetonitrile/water) to obtain the title compound (0.42 g) as a white solid.

Workup

  1. customThe reaction mixture was quenched with water (50 mL)
  2. extractionextracted with EtOAc (3×25 mL)
  3. washThe combined organic layers were washed with brine solution
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by reverse phase combiflash column chromatography (C18; eluent: 10-100% acetonitrile/water)

Sources & evidence

ORD record
ord-e1404cdf8e9e40ba8274d0f7f957f561
Source dataset
uspto-grants-2015_09
Patent number
US09133147B2

Reaction notes

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