Sodium triacetoxyborohydride → HCID 68676597, compound

HRID 1158511Notes

Reaction equation

HRID 1158511 reaction equation
[CH2:1]([C@@:8]([OH:28])([C:12]([N:14]1[C@H:18]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[CH2:25][C@H:17]2[O:16][C:15]1([CH3:27])[CH3:26])=[O:13])[CH2:9][CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][O:30][C:31]([NH:33][C@H:34]([C:39]([NH:41][NH2:42])=[O:40])[C:35]([CH3:38])([CH3:37])[CH3:36])=[O:32].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1>[CH3:29][O:30][C:31](=[O:32])[NH:33][C@H:34]([C:39]([NH:41][NH:42][CH2:10][CH2:9][C@:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([OH:28])[C:12]([N:14]1[C@H:18]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[CH2:25][C@H:17]2[O:16][C:15]1([CH3:27])[CH3:26])=[O:13])=[O:40])[C:35]([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10679660N-(Methoxycarbonyl)-3-methyl-L-valine hydrazideHCID 44819177HCID 44819177, compound

Product 1

HCID 68676597HCID 68676597, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-3-Benzyl-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3 aH-indeno[1,2-d]oxazol-3-yl)-3-hydroxy-4-oxo-butyraldehyde (21h) (0.082 g, 0.21 mmol) and [N-(methoxycarbony)-L-tert-leucinyl]hydrazine (0.048 g, 0.23 mmol, prepared as reported JMC, 41, 3387, 1998) in dry THF (10 mL) was stirred for 3 h and [the LCMS (ESI+) shows 565 (M+)], then Na(OAc)3BH (0.137 g, 0.64 mmol) was added and stirred overnight. The reaction mixture was quenched with water and evaporated. The residue was dissolved in dichloromethane and washed with water, brine and dried. The crude product was analysed by LCMS (ESI+) which showed 567 (M+) the title compound with a minor quantity of the compound lacking the protection group on the indanol moiety [MS (ESI+): 527 (M+)]. This mixture was alkylated by the next step without purification.

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with water
  3. customevaporated
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water, brine
  6. customdried
  7. customThis mixture was alkylated by the next step without purification

Sources & evidence

ORD record
ord-c9fb87735e8542d8873517f02b2081a3
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

Loading…