Nitrogen → Benzenebutanoicacid,b-[[(1,1-diMethylethoxy)carbonyl]aMino]-2,4,5-trifluoro-,Methylester,(bR)-

HRID 2061006Notes

Reaction equation

HRID 2061006 reaction equation
[CH3:1][O:2][C:3](=[O:24])/[CH:4]=[C:5](\[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])/[CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15].N#N>C1COCC1>[CH3:1][O:2][C:3](=[O:24])[CH2:4][C@H:5]([NH:16][C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[CH:9][C:8]=1[F:15]

Participants

4

Reactant 2

HCID 947NitrogenHCID 468365771234321-77-7

Product 1

HCID 11359981Benzenebutanoicacid,b-[[(1,1-diMethylethoxy)carbonyl]aMino]-2,4,5-trifluoro-,Methylester,(bR)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.28 g (3.71 mmol) of (Z)-Methyl-3-[N-(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)but-2-enoate of Example 3, 2.2 mg TangPhosRh(COD)BF4 and 10 mL THF were charged to a pressure bomb under N2 atmosphere. The N2 atmosphere was replaced by H2 (10 bars). The mixture was stirred at rt for 18 h. The reaction solution was passed through a silica gel pad and evaporated to dryness. The reaction gave quantitative yield and 99.0% ee. 1H NMR (300 MHz, CDCl3) 7.10-7.00 (m, 1H), 6.95-6.85 (m, 1H), 5.10 (m, 1H), 4.20-4.10 (m, 1H), 3.70 (s, 3H), 2.85 (m, 1H), 2.60-2.50 (m, 1H), 1.39 (s, 9H)

Workup

  1. customevaporated to dryness
  2. customThe reaction gave quantitative yield and 99.0% ee

Sources & evidence

ORD record
ord-ab175d570283404a8a5a82abe48202cf
Source dataset
uspto-grants-2012_10
Patent number
US08278486B2

Reaction notes

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