Triethylamine → HCID 11408870, compound

HRID 1071399Notes

Reaction equation

HRID 1071399 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][O:7][CH2:8][C@@H:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:10](O)=[O:11].Cl.[CH3:31][O:32][NH:33][CH3:34].C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:27][C:24]([F:25])([F:26])[C:22]1[CH:21]=[C:5]([CH:4]=[C:3]([C:2]([F:28])([F:1])[F:29])[CH:23]=1)[CH2:6][O:7][CH2:8][C@@H:9]([NH:13][C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[C:10]([N:33]([O:32][CH3:31])[CH3:34])=[O:11]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11281856HCID 11281856, compound

Product 1

HCID 11408870HCID 11408870, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-3-{3,5-bis(trifluoromethyl)benzyloxy}-2-tert-butoxycarbonylaminopropionic acid (76.6 g, 176 mmol), N-methoxy-N-methylamine hydrochloride (18.53 g, 190 mmol) and triethylamine (25.6 mL, 190 mmol) in CH2Cl2 (400 mL) was added WSC.HCl (36.4 g, 190 mmol). The mixture was stirred at room temperature for 20 hours, washed with water and saturated brine in order. The organic extract was dried over sodium sulfate anhydride. Sodium sulfate was filtered off and the solvent was removed by evaporation from the filtrate under reduced pressure to give (2R)-3-(3,5-bis(trifluoromethyl)benzyloxy)-2-tert-butoxycarbonylamino-N-methoxy-N-methylpropionamide (76.4 g, 92%) as a pale brown oil.

Workup

  1. washwashed with water and saturated brine in order
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate anhydride
  4. filtrationSodium sulfate was filtered off
  5. customthe solvent was removed by evaporation from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-07160003d2aa4d61a268b306cc4d29ce
Source dataset
uspto-grants-2005_06
Patent number
US06906074B2

Reaction notes

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