1,2-Dichloroethane → HCID 10834770, compound

HRID 879237Notes

Reaction equation

HRID 879237 reaction equation
C(Cl)CCl.C(N(CC)CC)C.[C:12]12([OH:22])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.[C:23]([NH:30][C@H:31]([C:39](O)=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>CN(C1C=CN=CC=1)C.ClCCl>[C:12]12([O:22][C:39](=[O:40])[C@H:31]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[NH:30][C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[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 641521-AdamantanolHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 10834770HCID 10834770, 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 316 mg (2.1 mmol) of 1-adamantanol 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 336 mg (43% 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-7213c1b36a4a4515bf8842b87acdd763
Source dataset
uspto-grants-2015_03
Patent number
US08987209B2

Reaction notes

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