Sodium cyanoborohydride → HCID 70197038, compound

HRID 456256Notes

Reaction equation

HRID 456256 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C@H:10]([NH:31][CH2:32][CH2:33][NH:34][C:35](=[O:55])[C@H:36]([CH:42]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[NH:37][C:38]([O:40][CH3:41])=[O:39])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH3-][C:57]#N.[Na+]>CC#N.CC(O)=O.C=O>[CH2:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:26][CH2:27][CH:28]([CH3:29])[CH3:30])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)(=[O:15])=[O:16])[C@H:10]([N:31]([CH3:57])[CH2:32][CH2:33][NH:34][C:35](=[O:55])[C@H:36]([CH:42]([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[NH:37][C:38]([O:40][CH3:41])=[O:39])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 68019352HCID 68019352, compound

Product 1

HCID 70197038HCID 70197038, compound

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolventHCID 22391770Acetonitrile aceticacidSolvent

Procedure

A mixture of N-(2-{[(3R,4R)-1-benzyl-4-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}pyrrolidin-3-yl]amino}ethyl)-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide (see Example 1, Step 12) (200 mg, 0.259 mmol) was dissolved in 20:1 MeCN—AcOH (3.5 mL) and 37% aqueous formaldehyde was added (0.68 mL) following by addition of NaBH3CN (49 mg, 0.78 mmol). The mixture was stirred at ambient temperature for 3 hours and quenched with water (50 mL). The mixture was extracted with CHCl3, the combined organic extracts were dried with Na2SO4 and evaporated. The residue was passed through silica gel layer eluting with 1% MeOH in CHCl3. The solvent was evaporated giving the desired compound. LC-MS APCI: m/z 785.3 [M+H]+.

Workup

  1. additionwas added (0.68 mL)
  2. customquenched with water (50 mL)
  3. extractionThe mixture was extracted with CHCl3
  4. dry with materialthe combined organic extracts were dried with Na2SO4
  5. customevaporated
  6. washeluting with 1% MeOH in CHCl3
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-33cc3e29070c48679991e6f7ec6143b9
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

Loading…