tert-Butyl 4-hydroxy-2-(hydroxymethyl)-2,3-dihydrobenzofuran-6-carboxylate → 4-[4-(Azetidine-1-carbonyl)-3-fluoro-phenoxy]-2-hydroxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester

HRID 1177197

Reaction equation

HRID 1177197 reaction equation
COC(C1C=C(OC2C=CC(S(C)(=O)=O)=CC=2)C=C2OC(C)CC=12)=O.[C:26]([O:30][C:31]([C:33]1[CH:43]=[C:42]([OH:44])[C:36]2[CH2:37][CH:38]([CH2:40][OH:41])[O:39][C:35]=2[CH:34]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27].[N:45]1([C:49]([C:51]2[CH:56]=[CH:55][C:54](F)=[CH:53][C:52]=2[F:58])=[O:50])[CH2:48][CH2:47][CH2:46]1>>[C:26]([O:30][C:31]([C:33]1[CH:43]=[C:42]([O:44][C:54]2[CH:55]=[CH:56][C:51]([C:49]([N:45]3[CH2:48][CH2:47][CH2:46]3)=[O:50])=[C:52]([F:58])[CH:53]=2)[C:36]2[CH2:37][CH:38]([CH2:40][OH:41])[O:39][C:35]=2[CH:34]=1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 3

HCID 25067321tert-Butyl 4-hydroxy-2-(hydroxymethyl)-2,3-dihydrobenzofuran-6-carboxylateHCID 59560289Azetidin-1-yl-(2,4-difluorophenyl)methanoneHCID 595604376-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

Product 1

HCID 595599294-[4-(Azetidine-1-carbonyl)-3-fluoro-phenoxy]-2-hydroxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1f, from 4-hydroxy-2-hydroxymethyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester (200f) and azetidin-1-yl-(2,4-difluoro-phenyl)-methanone. 1H NMR (400 MHz, CDCl3) δ 1.57 (s, 9 H) 2.26-2.38 (m, 2 H) 3.06-3.17 (m, 1 H) 3.67-3.78 (m, 1 H) 3.81-3.90 (m, 1 H) 4.09-4.18 (m, 3 H) 4.18-4.25 (m, 2 H) 4.92-5.02 (m, 1 H) 6.63-6.68 (m, 1 H) 6.78 (dd, J=8.59, 2.27 Hz, 1 H) 7.21 (d, J=1.26 Hz, 1 H) 7.49-7.56 (m, 1 H) 8.02 (s, 1 H); LCMS for C24H24FNO6 m/z 444.00 (M+H)+.

Sources & evidence

ORD record
ord-5ac0ff317db34c2488eb9836668a43d2
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Linked notes

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