Acetic Acid → HCID 136313965, compound

HRID 64516Notes

Reaction equation

HRID 64516 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[S:10][C:9]([C:15]3[S:16][CH2:17][CH:18]([C:20]([OH:22])=[O:21])[N:19]=3)=[N:8][C:7]=1[CH:6]=[CH:5]2.[C:23](O)(C(F)(F)F)=O.[N+](=C)=[N-].CC(O)=O>CC#N.CO.CCOCC>[CH3:23][O:21][C:20]([CH:18]1[CH2:17][S:16][C:15]([C:9]2[S:10][C:11]3[C:12]4[C:4](=[CH:3][C:2]([OH:1])=[CH:14][CH:13]=4)[CH:5]=[CH:6][C:7]=3[N:8]=2)=[N:19]1)=[O:22]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 9550Diazomethane2×HCID 1363139622-(7-Hydroxynaphtho[2,1-d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Product 1

HCID 136313965HCID 136313965, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

2-(7-Hydroxynaphtho[2,1-d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid (8 mg, 24 umol) was suspended in a mixture of MeCN and MeOH and acidified to pH<3 by the addition of TFA. The solution was treated with a solution of diazomethane in ether until the yellow color persisted. Excess diazomethane was neutralized by the addition of AcOH, the ether removed under reduced pressure, and the desired product (3.3 mg) isolated as a yellow solid by preparative HPLC eluting with 5→100% MeCN in NH4OAc, followed by lyophilization. Calcd for C16H13N2O3S2 (M+H): 345.0. found 345.

Workup

  1. customthe ether removed under reduced pressure

Sources & evidence

ORD record
ord-dbf87ff8b4014d2ea744d63306e92935
Source dataset
uspto-grants-2016_09
Patent number
US09447450B2

Reaction notes

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