1,2-Dichloroethane → HCID 12021269, compound

HRID 1058315Notes

Reaction equation

HRID 1058315 reaction equation
C(Cl)CCl.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:21][N:22]2[CH2:25][CH:24]([OH:26])[CH2:23]2)=[C:10]([CH:20]=1)[CH2:11][NH:12][C:13](=[O:19])[C@@H:14]1[CH2:18][CH2:17][CH2:16][NH:15]1.[OH:27][C:28]1([C:41](O)=[O:42])[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[OH:27][C:28]1([C:41]([N:15]2[CH2:16][CH2:17][CH2:18][C@H:14]2[C:13]([NH:12][CH2:11][C:10]2[CH:20]=[C:6]([Cl:5])[CH:7]=[CH:8][C:9]=2[CH2:21][N:22]2[CH2:25][CH:24]([OH:26])[CH2:23]2)=[O:19])=[O:42])[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:34]=2[C:35]2[C:40]1=[CH:39][CH:38]=[CH:37][CH:36]=2

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 10087FlurenolHCID 181649HOAtHCID 12021270HCID 12021270, compound

Product 1

HCID 12021269HCID 12021269, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (49.5, 0.26 mmol) was added to a stirred mixture of N-{5-chloro-2-[(3-hydroxyazetidin-1-yl)methyl]benzyl}-L-prolinamide (55.8 mg, 0.17 mmol), 9-hydroxy-9-H-fluoren-9-ylcarboxylic acid (40.9 mg, 0.18 mmol) and HOAT (11.7 mg, 0.086 mmol) in DMF (1.25 mL). After 16 h the mixture was concentrated and the residue was partitioned between EtOAc and 10% NaHCO3. The organic layer was washed with water and brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography on silica (ammonia saturated CHCl3/MeOH, 98:2) to give the title compound as a glass: HRMS (FAB) calcd C30H31ClN3O4 (M+1) 554.1817, found 554.1855.

Workup

  1. concentrationAfter 16 h the mixture was concentrated
  2. customthe residue was partitioned between EtOAc and 10% NaHCO3
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by chromatography on silica (ammonia saturated CHCl3/MeOH, 98:2)

Sources & evidence

ORD record
ord-01baeb7a91e94c5792c16a05cf681591
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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