1,2-Dichloroethane → HCID 57699995, compound

HRID 1009959Notes

Reaction equation

HRID 1009959 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]1(O)[CH2:27][CH2:26][CH2:25][CH2:24]1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH:23]1([O:11][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 7298CyclopentanolHCID 57699958HCID 57699958, compound

Product 1

HCID 57699995HCID 57699995, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-tert-Butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid (2.53 g, 7.6 mmol) in DCM (50 ml) at 0° C. was added cyclopentanol (1.39 ml, 15.3 ml), EDC (1.61 g, 8.4 mmol) and DMAP (0.093 g, 0.76 mmol). The reaction mixture was stirred for 16 hours at room temperature before evaporation under reduced pressure. The crude residue was dissolved in ethyl acetate (100 ml) and washed with 1M HCl, 1M Na2CO3 and brine. The organic layer was then dried over magnesium sulphate and evaporated under reduced pressure. The product was purified by column chromatography using ethyl acetate/heptane (1:4) to give 2.24 g, 73% yield of title compound. LCMS purity 100%, m/z 402.5 [M++H], 1H NMR (300 MHz, CDCl3), δ: 5.20 (1H, d, J=6.3 Hz), 5.15 (1H, m), 4.20 (1H, m), 3.6 (2H, m), 2.00 (1H, m), 1.95-1.55 (9H, bm), 1.40 (9H,s), 0.85 (9H,s), 0.10 (6H,s).

Workup

  1. washwashed with 1M HCl, 1M Na2CO3 and brine
  2. dry with materialThe organic layer was then dried over magnesium sulphate
  3. customevaporated under reduced pressure
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-ea23bc26a053489b89c995a2cf6a1a37
Source dataset
uspto-grants-2011_07
Patent number
US07973181B2

Reaction notes

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