1,2-Dichloroethane → 1,1-dimethylethyl (1S,4S)-5-(3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

HRID 2098462Notes

Reaction equation

HRID 2098462 reaction equation
[CH3:1][C:2]([CH3:19])([CH3:18])[C@@H:3]([C:15]([OH:17])=O)[NH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[C@H:20]12[CH2:26][C@H:23]([NH:24][CH2:25]1)[CH2:22][N:21]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O>[CH3:18][C:2]([CH3:1])([CH3:19])[C@@H:3]([C:15]([N:24]1[CH2:25][C@@H:20]2[CH2:26][C@H:23]1[CH2:22][N:21]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:17])[NH:4][C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:6]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 9899995(2S)-2-(((benzyloxy)carbonyl)amino)-3,3-dimethylbutanoic acidHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 672158231,1-dimethylethyl (1S,4S)-5-(3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylateYield 100.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valine (1.55 g, 5.84 mmol), 1,1-dimethylethyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1.1 g, 5.56 mmol), EDC (1.28 g, 111 mmol), HOBt (150 mg, 1.11 mmol), NMM (1.69 g, 16.7 mmol) in CH2Cl2 (20 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and CH2Cl2. The two layers were separated; the organic dried over anhydrous Na2SO4 and concentrated to give the title compound (2.5 g) as a pale yellow solid. LCMS (m/z): 446.2 (M+H).

Workup

  1. customThe two layers were separated
  2. dry with materialthe organic dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-86c56571c9ed4f85a185387547788061
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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