1,3-Benzodioxole-5-carbonyl chloride → (R)-methyl 2-(benzo[d][1,3]dioxole-6-carboxamido)-4-methylpentanoate

HRID 1644021Notes

Reaction equation

HRID 1644021 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](Cl)=[O:11])=[CH:9][C:4]=2[O:3][CH2:2]1.Cl.[CH3:14][O:15][C:16](=[O:23])[C@@H:17]([CH2:19][CH:20]([CH3:22])[CH3:21])[NH2:18]>>[O:3]1[C:4]2[CH:9]=[C:8]([C:10]([NH:18][C@H:17]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:16]([O:15][CH3:14])=[O:23])=[O:11])[CH:7]=[CH:6][C:5]=2[O:1][CH2:2]1

Participants

3

Reactant 2

HCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 11600782D-Leucine Methyl Ester Hydrochloride

Product 1

HCID 797901(R)-methyl 2-(benzo[d][1,3]dioxole-6-carboxamido)-4-methylpentanoateYield 83%

Procedure

Prepared in a similar manner to example 1 using benzo[d][1,3]dioxole-5-carbonyl chloride and D-leucine methyl ester hydrochloride. Yield: 83%. 1H NMR (500 MHz, CDCl3): δ 0.98 (m, 6H); 1.63-1.67 (m, 1H); 1.71-1.76 (m, 2H); 3.76 (s, 3H); 4.83 (m, 1H); 6.03 (s, 2H); 6.38 (d, 1H); 6.83 (d, 1H); 7.32 (s, 1H); 7.33 (d, 1H). MS (M+H, 294). m.p: 89-90° C.

Sources & evidence

ORD record
ord-e43187fd2f9947f6be8033ee8af150bc
Source dataset
uspto-grants-2012_02
Patent number
US08124121B2

Reaction notes

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