4-Acetoxy-3-fluorobenzoic acid → Pivalic acid (R)-6-{2-[ethyl(3-fluoro-4-hydroxybenzoyl)amino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

HRID 1434170Notes

Reaction equation

HRID 1434170 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[C@@H:14]1[CH2:23][CH2:22][C:21]2[CH:20]=[C:19]([O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[CH:18]=[CH:17][C:16]=2[CH2:15]1)[CH3:2].C([O:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][C:36]=1[F:44])(=O)C.C(OC1C=CC(C(CCNC2C=C(OC)C(OC)=CC=2[C@@H]2CCC3C=C(OC(=O)C(C)(C)C)C=CC=3C2)=O)=CC=1F)(=O)C>>[CH2:1]([N:3]([C:39](=[O:40])[C:38]1[CH:42]=[CH:43][C:35]([OH:34])=[C:36]([F:44])[CH:37]=1)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[C@@H:14]1[CH2:23][CH2:22][C:21]2[CH:20]=[C:19]([O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[CH:18]=[CH:17][C:16]=2[CH2:15]1)[CH3:2]

Participants

4

Reactant 3

HCID 193653054-Acetoxy-3-fluorobenzoic acidHCID 57934541pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 86605257pivalic acid (R)-6-{2-[(4-acetoxy-3-fluorobenzoyl)ethylamino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 57934194Pivalic acid (R)-6-{2-[ethyl(3-fluoro-4-hydroxybenzoyl)amino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester and 4-acetoxy-3-fluorobenzoic acid according to an analogous synthetic method to Preparation Example 154, pivalic acid (R)-6-{2-[(4-acetoxy-3-fluorobenzoyl)ethylamino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (537 mg) was used according to an analogous synthetic method to Preparation Example 155 to provide the title compound (298 mg).

Workup

  1. customwas used according to an analogous synthetic method to Preparation Example 155

Sources & evidence

ORD record
ord-8eb321f94e5f407b9cff1bbb24c8ea83
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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