Triethylamine → 4-nitrophenyl {(2S)-4-[1-(3,4-dichlorophenyl)ethyl]morpholin-2-yl}methylcarbamate

HRID 1371396Notes

Reaction equation

HRID 1371396 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([N:13]2[CH2:18][CH2:17][O:16][C@@H:15]([CH2:19][NH2:20])[CH2:14]2)[CH3:12])[CH:7]=[CH:8][C:9]=1[Cl:10].C(N(CC)CC)C.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:30]>ClCCl>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([N:13]2[CH2:18][CH2:17][O:16][C@@H:15]([CH2:19][NH:20][C:29](=[O:30])[O:31][C:32]3[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=3)[CH2:14]2)[CH3:12])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 690592951-{(2S)-4-[1-(3,4-Dichlorophenyl)ethyl]morpholin-2-yl}methanamine Dihydrochloride

Product 1

HCID 690668024-nitrophenyl {(2S)-4-[1-(3,4-dichlorophenyl)ethyl]morpholin-2-yl}methylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Intermediate 33 (0.724 g) in dichloromethane (5 ml) was treated with triethylamine (1.14 ml), forming a slurry which was added portion-wise over 5 min to a solution of 4-nitrophenyl chloroformate (0.444 g) in anhydrous dichloromethane (5 ml) at 0° C. under nitrogen. The stirring solution was allowed to warm to room temperature over 2 h, then filtered; the filtrate was purified directly by chromatography on silica gel (Biotage 90 g column), eluting with 35–40% ethyl acetate in cyclohexane, and appropriate fractions evaporated in vacuo to give the title compound (Isomer I) as an opaque yellow film (0.202 g).

Workup

  1. customforming a slurry which
  2. filtrationfiltered
  3. customthe filtrate was purified directly by chromatography on silica gel (Biotage 90 g column)
  4. washeluting with 35–40% ethyl acetate in cyclohexane, and appropriate fractions
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a2a9aca2e821444f85bfd0159f51b4e1
Source dataset
uspto-grants-2007_01
Patent number
US07157457B2

Reaction notes

Loading…