Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate → [2-(4-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}phenyl)-1,3-thiazol-5-yl]acetic acid

HRID 2076641Notes

Reaction equation

HRID 2076641 reaction equation
Br[CH2:2][C:3]1[C:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:7]([O:16]C(OC(C)(C)C)=O)[C:6]([C:24]([F:27])([F:26])[F:25])=[CH:5][CH:4]=1.C([CH:31]([C:35]1[S:39][C:38]([C:40]2[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][CH:41]=2)=[N:37][CH:36]=1)[C:32]([O-:34])=[O:33])C=C>>[C:12]([O:11][C:9]([C:8]1[C:7]([OH:16])=[C:6]([C:24]([F:25])([F:27])[F:26])[CH:5]=[CH:4][C:3]=1[CH2:2][O:46][C:43]1[CH:42]=[CH:41][C:40]([C:38]2[S:39][C:35]([CH2:31][C:32]([OH:34])=[O:33])=[CH:36][N:37]=2)=[CH:45][CH:44]=1)=[O:10])([CH3:13])([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 67119234Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoateHCID 136389263Allyl[2-(4-hydroxyphenyl)-1,3-thiazol-5-yl]acetate

Product 1

HCID 67119123[2-(4-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}phenyl)-1,3-thiazol-5-yl]acetic acidYield 9%

Procedure

According to a method similar to Example (2-3), Example (33-5) and Example (11-7), from tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate (314 mg, 0.69 mmol) obtained in Example (28-5) and allyl[2-(4-hydroxyphenyl)-1,3-thiazol-5-yl]acetate (190 mg, 0.69 mmol) obtained in Example (30-2), the title compound was obtained as a colorless powder (33 mg, three-step total yield: 9%).

Sources & evidence

ORD record
ord-ef9f6321ff8b458ca3087758faf40b6a
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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