1,2-Dichloroethane → HCID 131732923, compound

HRID 2168838Notes

Reaction equation

HRID 2168838 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].[NH:28]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C@H:29]([C:38]([OH:40])=[O:39])[CH2:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34].CN1CCOCC1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C.CN(C=O)C>[NH:28]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C@H:29]([C:38]([OH:40])=[O:39])[CH2:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34].[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

8

Reactant 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 1110824-tert-Butyl hydrogen N-((phenylmethoxy)carbonyl)-L-aspartateHCID 131732921HCID 131732921, compound

Product 1

HCID 131732923HCID 131732923, compoundYield 66.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3-(1-naphtyl)-L-alanine-Val-OAllyl (0.394 g, 1.11 mmol) was solvated in CH2Cl2 (1.5 mL) and DMF (3 ml) followed addition of Z-Asp(OtBu)-OH (0.369 g, 1.03 eq), DMAP (14.8 mg, 0.11 eq) and 4-methylmorpholine (0.125 ml, 1.02 eq), then EDC (0.221 g, 1.04 eq). The vial was rinsed with 0.5 ml of dichloromethane. The mixture was stirred for 2 hours at room temperature. Then it was extracted using CH2Cl2/brine. The organic layer was dried over MgSO4, filtered off and concentrated. The obtained residue was purified on silica using a gradient EtOAc/Hex (0 to 80%) to get 0.516 g of the desired compound.

Workup

  1. washThe vial was rinsed with 0.5 ml of dichloromethane
  2. extractionThen it was extracted
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered off
  5. concentrationconcentrated
  6. customThe obtained residue was purified on silica using a gradient EtOAc/Hex (0 to 80%)

Sources & evidence

ORD record
ord-fdb71daeb41c4911b9b1c6ffb5f0ead9
Source dataset
uspto-grants-2015_06
Patent number
US09045524B2

Reaction notes

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