1,2-Dichloroethane → HCID 66836374, compound

HRID 879238Notes

Reaction equation

HRID 879238 reaction equation
C(Cl)CCl.C(N(CC)CC)C.[C:12]12([CH2:22][OH:23])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.[C:24]([NH:31][C@H:32]([C:40](O)=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>CN(C1C=CN=CC=1)C.ClCCl>[C:12]12([CH2:22][O:23][C:40](=[O:41])[C@H:32]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[NH:31][C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH2:19][CH:18]3[CH2:17][CH:16]([CH2:15][CH:14]([CH2:20]3)[CH2:13]1)[CH2:21]2

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 66836374HCID 66836374, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1192 mg (6.2 mmol) of EDC, 578 μl (4.1 mmol) of triethylamine, 345 mg (2.8 mmol) of DMAP, and 345 mg (2.1 mmol) of 1-adamantylmethanol were added at RT to a solution of 500 mg (1.89 mmol) of N-Boc-L-phenylalanine in 25 ml dichlormethane. The reaction composition was stirred overnight, then diluted with 50 ml dichlormethane and successively washed in a solution of 10% of aqueous citric acid, water, and saturated saline. The organic phase was dried over magnesium sulphate and then evaporated, and the residue purified with preparative HPLC. The yield was 769 mg (90% o. th.) of the title compound.

Workup

  1. washsuccessively washed in a solution of 10% of aqueous citric acid, water, and saturated saline
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. customevaporated
  4. customthe residue purified with preparative HPLC

Sources & evidence

ORD record
ord-fafd13ecb02445468ee9a7db856432dd
Source dataset
uspto-grants-2015_03
Patent number
US08987209B2

Reaction notes

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