Sodium cyanoborohydride → HCID 69221574, compound

HRID 133827Notes

Reaction equation

HRID 133827 reaction equation
[CH:1]([C@@H:3]([N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:4]([CH3:12])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:5])=O.[CH2:22]([O:24][C:25](=[O:45])[C:26]([CH3:44])=[C:27](CC)[CH:28]([N:32]([C:34](=[O:41])[CH:35]([NH2:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[CH3:33])[CH:29]([CH3:31])[CH3:30])[CH3:23].C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[C:16]([O:15][C:14]([N:13]([CH3:21])[C@@H:3]([C:4]([CH3:12])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:5])[CH2:1][NH:40][C@H:35]([C:34]([N:32]([CH3:33])[C@@H:28]([CH:29]([CH3:31])[CH3:30])/[CH:27]=[C:26](\[CH3:44])/[C:25]([O:24][CH2:22][CH3:23])=[O:45])=[O:41])[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:20])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 86596610HCID 86596610, compoundHCID 86596611HCID 86596611, compound

Product 1

HCID 69221574HCID 69221574, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

To a stirred slurry of tert-butyl (1S)-1-formyl-2-methyl-2-phenylpropyl(methyl) carbamate (104 mg, 0.40 mmole, Reference Example 19) with ethyl 4-[(2-Amino-3,3-dimethyl-butyryl)-methyl-amino]-2,5-dimethyl-hex-2-enoic acid ethyl ester (122 mg, 0.40 mmole) in MeOH (2.5 ml), a solution of zinc chloride (32.7 mg, 0.6 eq) and sodium cyanoborohydride (34.4 mg, 0.48 mmol) in MeOH (2.5 ml) is added over 5 minutes at room temperature. The resulting mixture is stirred for 15-24 hours at room temperature under an inert atmosphere. After concentration, the residue is taken up in ethylacetate, washed with sodium bicarbonate. The aqueous phase is extracted with ethylacetate. The combined organic layers is washed with brine, dried and is chromatographed (silica gel, flash column) to give a white solid. (0.164 mg, 81%) M.W. 587.8 [M+H] 588.3

Workup

  1. concentrationAfter concentration
  2. washwashed with sodium bicarbonate
  3. extractionThe aqueous phase is extracted with ethylacetate
  4. washThe combined organic layers is washed with brine
  5. customdried
  6. customis chromatographed (silica gel, flash column)
  7. customto give a white solid

Sources & evidence

ORD record
ord-56a6a7ea371e444cb9eaea450076de41
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Reaction notes

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