Water → 2-((1S,4S)-4-((tert-butoxycarbonyl)amino)-1-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)acetic acid

HRID 1747129Notes

Reaction equation

HRID 1747129 reaction equation
[OH:1][CH2:2][CH2:3][C@@:4]1([C:17]([N:19]2[CH2:28][CH2:27][C:26]3[N:25]=[CH:24][C:23]([C:29]([F:32])([F:31])[F:30])=[CH:22][C:21]=3[CH2:20]2)=[O:18])[CH2:8][C@H:7]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:5]1.[OH2:33]>CC(C)=O>[C:12]([O:11][C:10]([NH:9][C@H:7]1[CH2:8][C@@:4]([CH2:3][C:2]([OH:33])=[O:1])([C:17]([N:19]2[CH2:28][CH2:27][C:26]3[N:25]=[CH:24][C:23]([C:29]([F:32])([F:31])[F:30])=[CH:22][C:21]=3[CH2:20]2)=[O:18])[CH:5]=[CH:6]1)=[O:16])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 962WaterHCID 86708129tert-butyl ((1S,4S)-4-(2-hydroxyethyl)-4-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)carbamate

Product 1

HCID 867081372-((1S,4S)-4-((tert-butoxycarbonyl)amino)-1-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the product of Example 1, Step D (508 mg, 1.12 mmol, 1 eq) in acetone (10 mL) at 0° C. was added Jones oxidation solution (0.46 mL, 1.23 mmol, 1.1 eq). After 2 hr, water was added, the aqueous was extracted with ethyl acetate, the organics combined, dried over MgSO4 and concentrated to afford the product of Step A that was used unpurified in the next step. Calculated for C22H26F3N3O5: 492.2 (M+23). found: 492.1.

Workup

  1. extractionthe aqueous was extracted with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1edbffe019204f8bad81e4b022778728
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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