Ethanol → HCID 68429693, compound

HRID 889283Notes

Reaction equation

HRID 889283 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[C:17]([F:27])[C:18]=1[N:19]1[CH2:23][C:22](=[O:24])[NH:21][S:20]1(=[O:26])=[O:25])[CH:15]=[C:14]([C:28]1[CH:29]=[C:30]([CH2:34][CH2:35][C:36]([OH:38])=[O:37])[CH:31]=[CH:32][CH:33]=1)[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:39](O)[CH3:40].OS(O)(=O)=O>C(OCC)(=O)C>[CH2:39]([O:37][C:36](=[O:38])[CH2:35][CH2:34][C:30]1[CH:31]=[CH:32][CH:33]=[C:28]([C:14]2[CH:13]=[CH:12][C:11]3[C:16](=[C:17]([F:27])[C:18]([N:19]4[CH2:23][C:22](=[O:24])[NH:21][S:20]4(=[O:26])=[O:25])=[C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:10]=3)[CH:15]=2)[CH:29]=1)[CH3:40]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 68431521HCID 68431521, compound

Product 1

HCID 68429693HCID 68429693, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The following examples are prepared using appropriate starting materials and general procedures described in Example 16 and Example 9 with the following exceptions. For 35-1, after step A of Example 9, the material is esterified by stirring 100 mg of 3-{3-[6-Benzyloxy-8-fluoro-7-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-naphthalen-2-yl]-phenyl}-propionic acid with 10 mL Ethanol and 0.2 mL H2SO4 for 3.5 hours. Ethyl acetate is added followed by evaporation of ethanol. The material is then extracted between ethyl acetate and water, and the organic layer is dried over sodium sulfate, filtered, concentrated to afford 3-{3-[6-Benzyloxy-8-fluoro-7-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-naphthalen-2-yl]-phenyl}-propionic acid ethyl ester and used in the next step, analogous to Example 9 step B, without purification. For 35-4, after step A of Example 9, the ester, 3-[6-Benzyloxy-8-fluoro-7-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-naphthalen-2-yl]-benzoic acid ethyl ester is hydrolyzed by addition of 0.84 mL of 1 M NaOH and heated in by microwave irradition for 30 min at 120° C. The aqueous layer is filtered and extracted with 1:1 ether hexanes. The aqueous layer is acidified and extracted 3 times with EtOAc, and the combined organic layers are dried over Mg2SO4, filtered and concentrated to afford 3-[6-Benzyloxy-8-fluoro-7-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-naphthalen-2-yl]-benzoic acid which is used in the next step without purification.

Workup

  1. customfollowed by evaporation of ethanol
  2. extractionThe material is then extracted between ethyl acetate and water
  3. dry with materialthe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0aff609630f14189a7d21ead14d7361a
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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