Acetic Acid → HCID 68749074, compound

HRID 1864791Notes

Reaction equation

HRID 1864791 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.[C:56]([O:60][C:61]([N:63]1[CH2:67][CH2:66][CH2:65][C@@H:64]1[CH2:68][NH:69][CH2:70][C:71]1[CH:76]=[CH:75][C:74]([F:77])=[CH:73][CH:72]=1)=[O:62])([CH3:59])([CH3:58])[CH3:57]>ClC(Cl)C.ClCCl>[C:56]([O:60][C:61]([N:63]1[CH2:67][CH2:66][CH2:65][C@@H:64]1[CH2:68][N:69]([CH2:70][C:71]1[CH:76]=[CH:75][C:74]([F:77])=[CH:73][CH:72]=1)[CH2:54][C:21]1[CH:22]=[C:23]([C:26]2[CH:53]=[CH:52][C:29]3[N:30]([C:33]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=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:24]=[CH:25][C:20]=1[F:19])=[O:62])([CH3:59])([CH3:57])[CH3:58]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 68746626HCID 68746626, compoundHCID 86616468HCID 86616468, compound

Product 1

HCID 68749074HCID 68749074, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (159 mg, 0.75 mmol) and acetic acid (36 mg, 0.6 mmol) were added to a mixture of 5-(4-fluoro-3-formylphenyl)-1-trityl-1H-benzotriazole (145 mg, 0.3 mmol) and (R)-2-[(4-fluoro-benzylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (111 mg, 0.36 mmol) and 4 angstrom molecular sieves in 5 mL of dichloroethane. The mixture was stirred at ambient temperature overnight, and then it was diluted with dichloromethane, and washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and concentrated to leave the crude product. Chromatography (elution with ethyl acetate/cyclohexane) provided 119 mg of product.

Workup

  1. washwashed with saturated sodium bicarbonate solution and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto leave the crude product
  6. washChromatography (elution with ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-61d76369185b449a97610f0925a05c22
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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