1,2-Dichloroethane → HCID 69656037, compound

HRID 857792Notes

Reaction equation

HRID 857792 reaction equation
FC(F)(F)C([O-])=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:17]2[CH:21]=[N:20][S:19][N:18]=2)=[C:13]([CH:16]=1)[CH2:14][NH3+:15].[C:22]([O:26][C:27]([NH:29][C@H:30]([CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[C:31]([N:33]1[CH2:40][CH2:39][CH2:38][C@H:34]1[C:35](O)=[O:36])=[O:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.C(Cl)CCl>CN(C=O)C>[C:22]([O:26][C:27]([NH:29][C@H:30]([CH:41]1[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]1)[C:31]([N:33]1[CH2:40][CH2:39][CH2:38][C@H:34]1[C:35]([NH:15][CH2:14][C:13]1[CH:16]=[C:9]([Cl:8])[CH:10]=[CH:11][C:12]=1[C:17]1[CH:21]=[N:20][S:19][N:18]=1)=[O:36])=[O:32])=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 9975432(2R)-2-Cyclohexyl-N-[(1,1-dimethylethoxy)carbonyl]glycyl-L-prolineHCID 21866199HCID 21866199, compound

Product 1

HCID 69656037HCID 69656037, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-chloro-2-(1,2,5-thiadiazol-3-yl)benzylammonium trifluoroacetate (40.9 mg, 0.13 mmol), 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-proline (prepared by standard peptide coupling protocols, 45.0 mg, 0.13 mmol), HOAt (22.5 mg, 0.17 mmol) and N-methylmorpholine (0.03 mL, 0.25 mmol) in DMF (0.5 mL) was added EDC (31.7 mg, 0.17 mmol). After 16 h the solution was partitioned between EtOAc and water. The organic phase was washed with brine, dried (Na2SO4) and reduced in vacuo. 1-{(2R)-2-[(tert-Butoxycarbonyl)amino]-2-cyclohexylethanoyl}-N-[5-chloro-2-(1,2,5-thiadiazol-3-yl)benzyl]-L-prolinamide was obtained as an oil. MS m/z=562.6.

Workup

  1. customAfter 16 h the solution was partitioned between EtOAc and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-b38a963f39c04bd2808272ab5bdb86c0
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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