4-Hydroxy-2-hydroxymethyl-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester → 4-(4-Dimethylcarbamoyl-3-fluoro-phenoxy)-2-hydroxymethyl-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester

HRID 1177237Notes

Reaction equation

HRID 1177237 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:44]=[C:43]([OH:45])[C:36]2[CH2:37][C:38]([CH2:41][OH:42])([CH3:40])[O:39][C:35]=2[CH:34]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27].[F:46][C:47]1[CH:57]=[C:56](F)[CH:55]=[CH:54][C:48]=1[C:49]([N:51]([CH3:53])[CH3:52])=[O:50]>>[C:26]([O:30][C:31]([C:33]1[CH:44]=[C:43]([O:45][C:56]2[CH:55]=[CH:54][C:48]([C:49](=[O:50])[N:51]([CH3:53])[CH3:52])=[C:47]([F:46])[CH:57]=2)[C:36]2[CH2:37][C:38]([CH2:41][OH:42])([CH3:40])[O:39][C:35]=2[CH:34]=1)=[O:32])([CH3:27])([CH3:28])[CH3:29]

Participants

4

Reactant 3

HCID 595599054-Hydroxy-2-hydroxymethyl-2-methyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl esterHCID 595604376-(4-Methanesulfonyl-phenoxy)-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl esterHCID 60637230HCID 60637230, compound

Product 1

HCID 595601644-(4-Dimethylcarbamoyl-3-fluoro-phenoxy)-2-hydroxymethyl-2-methyl-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-methyl-2,3-dihydro-benzofuran-6-carboxylic acid tert-butyl ester (227c) and 2,4-difluoro-N,N-dimethyl-benzamide. 1H NMR (400 MHz, CDCl3) δ 7.36 (t, J=8.08 Hz, 1 H) 7.24 (s, 1 H) 7.20 (d, J=1.26 Hz, 1 H) 6.78 (dd, J=8.59, 2.27 Hz, 1 H) 6.67 (dd, J=10.61, 2.27 Hz, 1 H) 3.67-3.73 (m, 1 H) 3.56-3.62 (m, 1 H) 3.08-3.18 (m, 4 H) 2.97 (d, J=1.52 Hz, 3 H) 2.77 (d, J=16.67 Hz, 1 H) 1.56 (s, 9 H) 1.43 (s, 3 H); LCMS for C24H28FNO6 m/z 446.00 (M+H)+.

Sources & evidence

ORD record
ord-61f39938553b4227bd3897ee5544d581
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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