Hexachloroacetone → (R)-N-[2-Chloro-4-(phenylsulphanyl)phenyl]-2-(t-butoxycarbonylamino)propanamide

HRID 2301062Notes

Reaction equation

HRID 2301062 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C(C(Cl)(Cl)Cl)=O.[C:30]([O:34][C:35]([NH:37][C:38]([CH3:43])([C:40]([OH:42])=O)C)=[O:36])([CH3:33])([CH3:32])[CH3:31].[Cl:44][C:45]1[CH:51]=[C:50]([S:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:49]=[CH:48][C:46]=1[NH2:47].[Cl-].[NH4+]>C(Cl)Cl.C(N(CC)CC)C>[Cl:44][C:45]1[CH:51]=[C:50]([S:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:49]=[CH:48][C:46]=1[NH:47][C:40](=[O:42])[C@H:38]([NH:37][C:35]([O:34][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:36])[CH3:43]

Participants

8

Reactant 5

HCID 8303HexachloroacetoneHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanineHCID 222872082-Chloro-4-phenylthioaniline

Product 1

HCID 69748591(R)-N-[2-Chloro-4-(phenylsulphanyl)phenyl]-2-(t-butoxycarbonylamino)propanamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Triphenylphosphine (0.0.612 g) was added to a cooled (−78° C.) solution of hexachloroacetone (0.18 ml) and N-t-butyloxycarbonyl-2-methylalanine (0.441 g) in dry DCM (15 ml) under argon. The resulting mixture was stirred at low temperature for 20 minutes. Then 2-chloro-4-(phenylsulphanyl)aniline (0.5 g) (Method 5) and dry triethylamine (0.33 ml) were added. The resulting mixture was slowly warmed to room temperature, under argon, before being stirred for 1 hour at room temperature. Saturated aqueous ammonium chloride solution (15 ml) was added and the mixture was extracted with DCM (2×50 ml). The organic extracts were combined, washed with brine and dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel column eluting with 2% ethyl acetate/DCM to give the title compound. NMR (CDCl3): 1.40-1.45 (m, 12H), 4.294.40 (m, 1H), 4.864.95 (m, 1H), 7.20-7.40 (m, 7H), 8.30-8.38 (m, 1H), 8.64 (brs, 1H); MS (ESP−): 405.

Workup

  1. stirringbefore being stirred for 1 hour at room temperature
  2. extractionthe mixture was extracted with DCM (2×50 ml)
  3. washwashed with brine
  4. customdried
  5. customVolatile material was removed by evaporation
  6. customthe residue was purified by chromatography on a silica gel column
  7. washeluting with 2% ethyl acetate/DCM

Sources & evidence

ORD record
ord-3ea91020a23e4b0ca79e015c8aaeee28
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

Loading…