Sodium triacetoxyborohydride → HCID 54338209, compound

HRID 1780805Notes

Reaction equation

HRID 1780805 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[CH3:15])=[O:6].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:33]([O:37][C:38]([NH:40][C@H:41]([CH:63]=O)[CH2:42][S:43][C:44]([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34]>ClCCCl>[C:33]([O:37][C:38]([NH:40][C@@H:41]([CH2:42][S:43][C:44]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[CH2:63][NH:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[CH3:15])=[O:6])=[O:39])([CH3:34])([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 64565863-amino-N-(2,3-dimethylphenyl)benzamideHCID 10388929N-Boc-S-trityl-(L)-cysteinal

Product 1

HCID 54338209HCID 54338209, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2 (0.28 g) in 12 mL of 1,2-dichloroethane at 0° C. was added sodium triacetoxyborohydride (0.36 g) and N-t-butyloxycarbonyl-S-(triphenyl- methyl)cysteinal (0.35 g). The cooling bath was removed and the mixture was stirred for 4 h at 20° C. The solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The ethyl acetate layer was extracted with 50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a foam. NMR (300 MHz, CDCl3) δ 8.17 (1H, b), 7.46-7.18 (15H, m), 6.60 (1H, m), 3.13(2H, m,), 2.45(3H, m), 2.30 (3H, s), 2.18 (3H, s), 1.42 (9H, s).

Workup

  1. customThe cooling bath was removed
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe ethyl acetate layer was extracted with 50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62f6a466590c4ce697af1f2b5e7f422b
Source dataset
uspto-grants-1997_05
Patent number
US05631280

Reaction notes

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