HCID 67099598, compound → HCID 57983572, compound

HRID 1868690Notes

Reaction equation

HRID 1868690 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:15][CH2:14][CH2:13][CH2:12]1)[C:7](=[O:16])[C:6]([C:17]([NH:19][CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])=[O:18])=[C:5]2[OH:28]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]1([CH2:12][CH2:13][CH2:14][CH2:15]1)[C:7](=[O:16])[C:6]([C:17]([NH:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])=[C:5]2[OH:28]

Participants

3

Reactant 1

HCID 67099598HCID 67099598, compound

Product 1

HCID 57983572HCID 57983572, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1,1-dimethylethyl N-((6′-chloro-4′-hydroxy-2′-oxo-2′H-spiro[cyclopentane-1,1′-naphthalen]-3′-yl)carbonyl)glycinate (0.2 g, 0.5 mmol) in 2 mL TFA was stirred at room temperature for 30 minutes, M+1=350. The mixture was concentrated and triturated in ether/hexane (10:1). The solid was filtered, washed with 10 mL ether/hexane (10:1), and dried under high vacuum to give 135 mg of the salt as an off-white solid. MS (m/z)=350 (M+H)+. Calculated for C17H16ClNO5 349.07.

Workup

  1. concentrationThe mixture was concentrated
  2. customtriturated in ether/hexane (10:1)
  3. filtrationThe solid was filtered
  4. washwashed with 10 mL ether/hexane (10:1)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-4075eb8dba854e36a2a7fa93518ab9d4
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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