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1,2-Dichloroethane → HCID 58017551, compound

HRID 1642761
Notes
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Reaction equation

HRID 1642761 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][C:10](=[O:13])[CH2:11][CH3:12])[C:3]=1[C:14]([CH3:20])([CH3:19])[CH2:15][C:16]([OH:18])=[O:17].[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([N:48]2[CH:52]=[N:51][N:50]=[N:49]2)=[C:26]([CH:47]=1)[CH2:27][NH:28][C:29]([C@H:31]1[N:35]([C:36](=[O:46])[C@@H:37]([C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=2)O)[N:34]=[CH:33][CH2:32]1)=[O:30].C(Cl)CCl>C(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][C:10](=[O:13])[CH2:11][CH3:12])[C:3]=1[C:14]([CH3:19])([CH3:20])[CH2:15][C:16]([O:18][C@H:37]([C:39]1[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=1)[C:36]([N:35]1[C@H:31]([C:29](=[O:30])[NH:28][CH2:27][C:26]2[CH:47]=[C:22]([Cl:21])[CH:23]=[CH:24][C:25]=2[N:48]2[CH:52]=[N:51][N:50]=[N:49]2)[CH2:32][CH:33]=[N:34]1)=[O:46])=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 44537923AZ-12971554HCID 57425266HCID 57425266, compound

Product 1

HCID 58017551HCID 58017551, compoundYield 92.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(2,4-dimethyl-6-(propionyloxy)phenyl)-3-methylbutanoic acid (160 mg, 0.57 mmol) and (S)—N-(5-chloro-2-(1H-tetrazol-1-yl)benzyl)-1-((R)-2-(4-fluorophenyl)-2-hydroxyacetyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (263 mg, 0.57 mmol) in DCM (3 mL) and DMF (3 mL) was added EDC (165 mg, 0.86 mmol) and DMAP (7 mg, 0.06 mmol). The clear colorless solution was stirred at rt for 48 h. The mixture was diluted with DCM and washed with water, 1M HCl and sat NaHCO3. The organic phase was dried, filtered, evaporated and purified by flash chromatography (DCM/EtOAc gradient from 4:1 to 2:1) to give (R)-2-((S)-5-(5-chloro-2-(1H-tetrazol-1-yl)benzylcarbamoyl)-4,5-dihydro-1H-pyrazol-1-yl)-1-(4-fluorophenyl)-2-oxoethyl 3-(2,4-dimethyl-6-(propionyloxy)phenyl)-3-methylbutanoate (380 mg, 92%) as a semisolid.

Workup

  1. washwashed with water, 1M HCl
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by flash chromatography (DCM/EtOAc gradient from 4:1 to 2:1)

Sources & evidence

ORD record
ord-94c7fe50ecda437e8ee5fb31e5e8aa2a
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08119673B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes