1,2-Dichloroethane → HCID 131732923, compound

HRID 2168840Notes

Reaction equation

HRID 2168840 reaction equation
[C:1]1([CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:17][C@H:18]([C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[CH:19]([CH3:21])[CH3:20].F[C:29]([C:32]([OH:34])=[O:33])(F)F.C(N(CC)[CH:39]([CH3:41])[CH3:40])(C)C.C1C=[CH:46][C:47]2N(O)N=N[C:48]=2[CH:49]=1.[CH2:54](Cl)CCl>CN(C=O)C>[NH:13]([C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:46][CH:47]=[CH:48][CH:49]=1)=[O:23])[C@H:12]([C:14]([OH:16])=[O:15])[CH2:29][C:32](=[O:33])[O:34][C:39]([CH3:41])([CH3:54])[CH3:40].[C:1]1([CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:17][C@H:18]([C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[CH:19]([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1317329253-(1-naphtyl)-L-alanine Val-OAllyl TFA

Product 1

HCID 131732923HCID 131732923, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3-(1-naphtyl)-L-alanine-Val-OAllyl TFA salt (1.515 g, 1 eq) in DMF (4.6 ml) was added N,N-diisopropyl ethyl amine (0.56 ml, 1 eq) and the mixture was stirred for 5 min, then added to a solution of Z-Asp(β-tert-butyl)-OH (1.045 g, 3.23 mmol) in 3 ml of DMF. The mixture was shilled at 0° C. HOBT anhydrous (0.437 g, 1 eq) was added followed with EDC (0.682 g; 1.1 eq) in DMF (2.3 ml, as a suspension), The vial of EDC was washed with DMF (2*1.6 ml) and was added to the solution. The mixture was stirred for 22 h (0° C. to RT). It was then diluted with EtOAc (60 ml), the organic layer was washed with citric acid 0.5 M (3*10 ml), then K2CO3 (7.5% w/w) (3*10 ml), then Brine (1*10 ml). The organic layer was dried with MgSO4, filtered off and the solvent was evaporated to dryness to get 1.88 g of the desired and clean compound, which was used for the next step as a crude compound.

Workup

  1. customwas shilled at 0° C
  2. washas a suspension), The vial of EDC was washed with DMF (2*1.6 ml)
  3. additionwas added to the solution
  4. stirringThe mixture was stirred for 22 h (0° C. to RT)
  5. additionIt was then diluted with EtOAc (60 ml)
  6. washthe organic layer was washed with citric acid 0.5 M (3*10 ml)
  7. dry with materialThe organic layer was dried with MgSO4
  8. filtrationfiltered off
  9. customthe solvent was evaporated to dryness
  10. customto get 1.88 g of the

Sources & evidence

ORD record
ord-fbb72973ced444618523287d9561c781
Source dataset
uspto-grants-2015_06
Patent number
US09045524B2

Reaction notes

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