HCID 52987736, compound → (R)-tert-Butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)oxazolidine-3-carboxylate

HRID 2357069Notes

Reaction equation

HRID 2357069 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[C:8]([C:21]([F:24])([F:23])[F:22])[CH:7]=1)=[O:5].[C:25]([O:29][C:30]([N:32]1[C@@:36]([CH3:40])([C:37](O)=[O:38])[CH2:35][O:34][C:33]1([CH3:42])[CH3:41])=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[CH3:41][C:33]1([CH3:42])[N:32]([C:30]([O:29][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:31])[C@@:36]([CH3:40])([C:37](=[O:38])[NH:2][CH2:3][C:4]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[C:8]([C:21]([F:22])([F:23])[F:24])[CH:7]=2)=[O:5])[CH2:35][O:34]1

Participants

3

Reactant 2

HCID 52987736HCID 52987736, compoundHCID 684532372-Amino-1-(4-(octyloxy)-3-(trifluoromethyl)phenyl)ethanone hydrochloride

Product 1

HCID 59384447(R)-tert-Butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)oxazolidine-3-carboxylate

Procedure

Synthesis of phenyl-thiazoles is described in Scheme 4. Reaction of benzyl or allyl alcohol with substituted 4-fluorobenzoic acid 1 afforded the substituted ether-benzoate 2. The substituted ether-benzoate 2 was then coupled with hydrazine to afford benzohydrazide 3. Reaction of benzohydrazide 3 with orthogonally protected amino acid 4 under HATU conditions followed by cyclization and deprotection (or vis versa) provided phenol 6 in good yield. Mitsunobu reaction of phenol 6 with desired alcohol followed by deprotection afforded the desired final compound 8. Reaction of the alcohol 8 with diethyl chlorophosphate followed by deprotection with TMSBr gave the corresponding phosphate.

Sources & evidence

ORD record
ord-87b0a1c2533a46c5bb314d3a3c842601
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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