Acetic Acid → HCID 66671553, compound

HRID 1171151Notes

Reaction equation

HRID 1171151 reaction equation
C([C@@H]1COC(=O)N1[C:14](=[O:36])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:22][C:21]=1[Cl:35])[CH2:16][CH:17]=O)C1C=CC=CC=1.[NH2:37][CH:38]1[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:47]([O:46][C:44]([N:41]1[CH2:42][CH2:43][CH:38]([N:37]2[CH2:17][CH2:16][C@@H:15]([CH2:19][C:20]3[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:22][C:21]=3[Cl:35])[C:14]2=[O:36])[CH2:39][CH2:40]1)=[O:45])([CH3:50])([CH3:48])[CH3:49]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 59515429(R)-4-((R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde

Product 1

HCID 66671553HCID 66671553, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a solution of (R)-4-((R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde (Preparation 10) (4.0 g, 7.6 mmol) and 4-Amino-1N-Boc-piperidine (1.5 g, 7.6 mmol) in CH2Cl2 (100 mL) with acetic acid (0.4 mL, 7.6 mmol) and stir the reaction 1 hr at room temperature. Treat the reaction with sodium triacetoxyborohydride (3.2 g, 15 mmol) and stir overnight at room temperature. Quench the reaction with water and separate the organic layer. Wash the organic with brine, dry over MgSO4, filter, and remove the solvent. Purify the crude by silica gel column chromatography using Hexanes:EtOAc to elute the pure product. Remove the solvent to afford 2.35 g (58%) of desired product. MS (m/e): 555 (M+Na+).

Workup

  1. customthe reaction 1 hr at room temperature
  2. additionTreat
  3. stirringstir overnight at room temperature
  4. customQuench
  5. customthe reaction with water
  6. customseparate the organic layer
  7. washWash the organic with brine
  8. dry with materialdry over MgSO4
  9. filtrationfilter
  10. customremove the solvent
  11. customPurify the crude by silica gel column chromatography
  12. washEtOAc to elute the pure product
  13. customRemove the solvent

Sources & evidence

ORD record
ord-781d96696ea847528d863698ee61236b
Source dataset
uspto-grants-2010_11
Patent number
US07829582B2

Reaction notes

Loading…