Benzaldehyde → HCID 58653133, compound

HRID 2357875Notes

Reaction equation

HRID 2357875 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:23][C:24]([C:26]2[C:27]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:25])[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH2:14][NH:13][C@H:12]([CH2:21][OH:22])[CH2:11]1)=[O:9].[CH:38](=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)CCl.C(Cl)Cl>[CH2:38]([N:13]1[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:10]([C:8]([C:7]2[CH:6]=[CH:5][C:4]([NH:23][C:24]([C:26]3[C:27]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:25])=[CH:3][C:2]=2[Cl:1])=[O:9])[CH2:11][C@H:12]1[CH2:21][OH:22])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58653120HCID 58653120, compound

Product 1

HCID 58653133HCID 58653133, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-biphenyl-2-carboxylic acid [3-chloro-4-(3-hydroxymethyl-2,3,4,5-tetrahydrobenzo[e][1,4]diazepine-1-carbonyl)-phenyl]-amide (1.02 g; 1.95 mmol) dissolved in ClCH2CH2Cl (11 mL) was added benzaldehyde (2.92 mmol) followed by sodium triacetoxyborohydride (0.824 g; 3.89 mmol) in one-portion and the reaction was stirred for 18 h at rt. The reaction was diluted with CH2Cl2, washed with H2O, dried over Na2SO4, filtered, and the solvent removed under reduced pressure to afford a crude residue which was purified by flash chromatography (SiO2) eluting with EtOAc-MeOH gradient to afford 0.949 g (81%) of the title compound as a white solid. [α]23D: −75° (c 1.4, MeOH); 1H NMR (300 MHz, CDCl3): δ 7.81-7.83 (d, 1H), 7.28-7.56 (m, 13H), 6.71-7.20 (m, 7H), 4.77-4.82 (m, 1H), 4.40-4.46 (m, 1H), 3.85-4.10 (m, 2H), 3.52-3.69 (m, 3H), 3.31-3.36 (m, 1H), 3.14 (s, 1H); LC/MS m/z 602 (M+1). Calcd for C33H32ClN3O3.0.88% H2O; C, 72.08; H, 5.31; N, 6.80; Cl, 6.91.

Workup

  1. washwashed with H2O
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customto afford a crude residue which
  6. customwas purified by flash chromatography (SiO2)
  7. washeluting with EtOAc-MeOH gradient

Sources & evidence

ORD record
ord-f8c242f465f94e1595a356e2b5458221
Source dataset
uspto-grants-2010_07
Patent number
US07763605B2

Reaction notes

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