Acetic Acid → HCID 117812696, compound

HRID 591299Notes

Reaction equation

HRID 591299 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][O:29][Si](C(C)(C)C)(C)C)=[CH:22][N:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][OH:29])=[CH:22][N:21]=1)[C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 123585374HCID 123585374, compound

Product 1

HCID 117812696HCID 117812696, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of di-tert-butyl (4R)—N-(tert-butoxycarbonyl)-4-{[5-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)pyridin-2-yl]methyl}-L-glutamate (140 mg, 0.23 mmol) in tetrahydrofuran (7 ml) was added acetic acid (80 μl, 1.40 mmol). The solution was cooled to 0° C., and tetra-n-butylammonium fluoride (1M in tetrahydrofuran, 674 μl) was added dropwise. The cooling bath was removed and the reaction was stirred overnight, then mixed with 1 N aqueous sodium hydrogen carbonate solution (20 ml), and extracted with dichloromethane (3×20 ml). The organic phases were washed with brine (10 ml), dried over sodium sulfate and concentrated in vacuo. The crude material was used without further purification.

Workup

  1. customThe cooling bath was removed
  2. additionmixed with 1 N aqueous sodium hydrogen carbonate solution (20 ml)
  3. extractionextracted with dichloromethane (3×20 ml)
  4. washThe organic phases were washed with brine (10 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude material was used without further purification

Sources & evidence

ORD record
ord-4d8189b895f94998b255dcc2e789d237
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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