Diisopropylethylamine → (3R)-ethyl 2-(tert-butoxycarbonylamino)-3,5-dimethylnon-8-enoate

HRID 1852200Notes

Reaction equation

HRID 1852200 reaction equation
Cl.[NH2:2][CH:3]([C@H:9]([CH2:17]C)[CH2:10][CH:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C:4]([O:6][CH2:7][CH3:8])=[O:5].CCN(C(C)C)C(C)C.[O:28](C(OC(C)(C)C)=O)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=O>C(Cl)Cl>[C:32]([O:31][C:29]([NH:2][CH:3]([C@H:9]([CH3:17])[CH2:10][CH:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:28])([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 86683258(3R)-ethyl 2-amino-3-ethyl-5-methylnon-8-enoate hydrochloride

Product 1

HCID 86683235(3R)-ethyl 2-(tert-butoxycarbonylamino)-3,5-dimethylnon-8-enoateYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (3R)-ethyl 2-amino-3-ethyl-5-methylnon-8-enoate hydrochloride (2.99 g, 10.77 mmole) in DCM (20 mL) was added DIPEA (1.08 mL, 10.77 mmole) followed by (BOC)2O (2.39 mL, 10.77 mmole) at room temperature. The reaction mass was stirred at room temperature for overnight. The reaction mass was diluted with DCM and washed with water. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by column chromotography (Silica gel, 20% ethyl acetate in pet-ether) to get 2.3 g, (62.5%) of (3R)-ethyl 2-(tert-butoxycarbonylamino)-3,5-dimethylnon-8-enoate as an oily liquid. MS: MS m/z 342.4 (M++1).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customevaporated under reduced pressure
  4. customto get crude compound
  5. customThe crude compound was purified by column chromotography (Silica gel, 20% ethyl acetate in pet-ether)

Sources & evidence

ORD record
ord-d9771bda81c743d494ff75a4061f774e
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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