Acetic Acid → HCID 68796575, compound

HRID 1864779Notes

Reaction equation

HRID 1864779 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:53]=[CH:52][C:29]3[N:30]([C:33]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[N:31]=[N:32][C:28]=3[CH:27]=2)=[CH:22][C:21]=1[CH:54]=O.[CH3:56][Si:57]([CH3:71])([CH3:70])[CH2:58][CH2:59][O:60][C:61]([N:63]1[CH2:68][CH2:67][CH:66]([NH2:69])[CH2:65][CH2:64]1)=[O:62].C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C.ClCCl>[CH3:56][Si:57]([CH3:71])([CH3:70])[CH2:58][CH2:59][O:60][C:61]([N:63]1[CH2:64][CH2:65][CH:66]([NH:69][CH2:54][C:21]2[CH:22]=[C:23]([C:26]3[CH:53]=[CH:52][C:29]4[N:30]([C:33]([C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)([C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)[C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[N:31]=[N:32][C:28]=4[CH:27]=3)[CH:24]=[CH:25][C:20]=2[F:19])[CH2:67][CH2:68]1)=[O:62]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68749290HCID 68749290, compoundHCID 86616468HCID 86616468, compound

Product 1

HCID 68796575HCID 68796575, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (890 mg, 4.2 mmol) and acetic acid (126 mg, 4.2 mmol) were added to a solution of 5-(4-fluoro-3-formylphenyl)-1-trityl-1H-benzotriazole (1.0 mg, 2.1 mmol) and 4-amino-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (760 mg, 3.1 mmol) in dichloroethane. The mixture was stirred at ambient temperature overnight, and then it was diluted with dichloromethane, and neutralized with careful addition of 1 M sodium carbonate solution. The layers were separated and the aqueous phase extracted with dichloromethane. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography provided 980 mg of product. LC/MS: Retention time, 3.27 and 3.34 min; (M+H)=712.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase extracted with dichloromethane
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto leave the crude product

Sources & evidence

ORD record
ord-6353660cf6c14f9885ce0653a75a5df2
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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