Methyl 3-Hydroxybenzoate → HCID 18930691, compound

HRID 658883Notes

Reaction equation

HRID 658883 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CS(O[CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])(=O)=O>>[C:23]([O:22][C:20]([NH:19][CH2:18][CH2:17][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 88068Methyl 3-HydroxybenzoateHCID 22605302tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate

Product 1

HCID 18930691HCID 18930691, compound

Procedure

Coupling of methyl 3-hydroxybenzoate with 2-(tert-butoxycarbonylamino)ethyl methanesulfonate following the method used in Example 9 gave methyl 3-(2-(tert-butoxycarbonylamino)ethoxy)benzoate as a light yellow oil. Yield (0.65 g, 84%): 1H NMR (400 MHz, CD3OD) δ 7.36 (t, J=8.0 Hz, 1H), 7.26 (t, J=8.0 Hz, 1H), 7.16 (ddd, J=8.4, 2.4, 0.8 Hz, 1H), 6.99 (ddd, J=8.0, 2.4, 0.8 Hz, 1H), 4.03 (t, J=5.6 Hz, 2H), 3.78 (s, 3H), 1.43 (s, 9H).

Sources & evidence

ORD record
ord-be42a10f0bda42bfbdb29b7a493a2a8c
Source dataset
uspto-grants-2011_12
Patent number
US08076516B2

Reaction notes

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