1,2-Dichloroethane → HCID 69655948, compound

HRID 857797Notes

Reaction equation

HRID 857797 reaction equation
C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.[C:15]([O:19][C:20]([NH:22][C@H:23]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[C:24]([N:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28](O)=[O:29])=[O:25])=[O:21])([CH3:18])([CH3:17])[CH3:16].[Cl:40][C:41]1[CH:42]=[CH:43][C:44]([C:49]2[N:50]=[N:51][S:52][CH:53]=2)=[C:45]([CH2:47][NH2:48])[CH:46]=1>CN(C=O)C>[C:15]([O:19][C:20]([NH:22][C@H:23]([CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1)[C:24]([N:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28]([NH:48][CH2:47][C:45]1[CH:46]=[C:41]([Cl:40])[CH:42]=[CH:43][C:44]=1[C:49]1[N:50]=[N:51][S:52][CH:53]=1)=[O:29])=[O:25])=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 9975432(2R)-2-Cyclohexyl-N-[(1,1-dimethylethoxy)carbonyl]glycyl-L-prolineHCID 21866164HCID 21866164, compound

Product 1

HCID 69655948HCID 69655948, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (0.388 g, 2.02 mmol), HOAt (0.275 g, 2.02 mmol), and 1-{(2R)-2-[(tert-butoxycarbonyl)amino]-2-cyclohexylethanoyl}-L-proline (prepared by standard peptide coupling protocols, 0.551 g, 1.55 mol) were added to a stirred solution of 1-[5-Chloro-2-(1,2,3-thiadiazol-4-yl)phenyl]methanamine (0.351 g, 1.555 mmol) in DMF (7.8 mL). After 16 h the mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo. The product was purified by flash chromatography on silica (eluting with an EtOAc/hexanes gradient, 1–100% EtOAc). 1-{(2R)-2-[(tert-Butoxycarbonyl)amino]-2-cyclohexylethanoyl}-N-[5-chloro-2-(1,2,3-thiadiazol-4-yl)benzyl]-L-prolinamide was obtained as a solid. MS m/z=562.6.

Workup

  1. customAfter 16 h the mixture was partitioned between EtOAc and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash chromatography on silica (
  6. washeluting with an EtOAc/hexanes gradient, 1–100% EtOAc)

Sources & evidence

ORD record
ord-55a0449bf4944b68aca1df815e48c9fc
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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