Sodium triacetoxyborohydride → HCID 66922886, compound

HRID 1622970Notes

Reaction equation

HRID 1622970 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16][C:17]([CH3:31])([C:19]([O:21][CH:22]3[CH2:30]C4C(=CC=CC=4)[CH2:23]3)=[O:20])[CH3:18])=[CH:10][CH:9]=2)[C:6](=[O:32])[CH:5]=[CH:4][C:3]=1[C:33](=[O:42])[C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=1[F:41].[CH3:43]C(C(OC(C)(C)C)=O)(C)N.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.CCOC(C)=O>[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16][C:17]([CH3:31])([C:19]([O:21][C:22]([CH3:30])([CH3:23])[CH3:43])=[O:20])[CH3:18])=[CH:10][CH:9]=2)[C:6](=[O:32])[CH:5]=[CH:4][C:3]=1[C:33](=[O:42])[C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=1[F:41]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 7019940tert-Butyl 2-methylalaninate2×HCID 66922813HCID 66922813, compound

Product 1

HCID 66922886HCID 66922886, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 2 (180 mg, 0.489 mmol) in THF (3 ml) was added tert-butyl 2-methylalaninate (Intermediate 8) (117 mg, 0.73 mmol), stirred for 30 minutes, and then NaBH(OAc)3 (310 mg, 1.467 mmol). The reaction was stirred for 24 hours, diluted with EtOAc and the organics washed with sat NaHCO3, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by preparative HPLC to provide the title compound (Intermediate 15) (120 mg, 48% yield).

Workup

  1. stirringThe reaction was stirred for 24 hours
  2. washthe organics washed
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b2391cef628446cfb7abdb44cb3325a5
Source dataset
uspto-grants-2014_07
Patent number
US08778953B2

Reaction notes

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