1,1-Dichloroethane → HCID 57672054, compound

HRID 1692095Notes

Reaction equation

HRID 1692095 reaction equation
ClC(Cl)C.[NH2:5][N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.C([C@@H]1COC(=O)N1[C:25](=[O:47])[C@H:26]([CH2:30][C:31]1[C:36]([Cl:37])=[CH:35][C:34]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:33][C:32]=1[Cl:46])[CH2:27][CH:28]=O)C1C=CC=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:39]([O:38][C:34]1[CH:33]=[C:32]([Cl:46])[C:31]([CH2:30][C@@H:26]2[CH2:27][CH2:28][N:5]([N:6]3[CH2:11][CH2:10][O:9][CH2:8][CH2:7]3)[C:25]2=[O:47])=[C:36]([Cl:37])[CH:35]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 20315N-AminomorpholineHCID 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 57672054HCID 57672054, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a mixture of dichloroethane (25 mL), N-aminomorpholine (0.204 g, 2 mmol), (R)-4-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde (1.064 g, 2 mmol) and sodium triacetoxyborohydride (1.266 g, 6 mmol) at room temperature for 12 hours. Bring the reaction to 60° C. and stir for 3 hours. Cool the reaction, dilute with dichloromethane, and wash with water. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify on silica with a 50 to 75% ethyl acetate in hexanes gradient to afford 0.07 g (80%) of the titled product. MS (m/z): 435 (M+).

Workup

  1. customBring the reaction to 60° C.
  2. stirringstir for 3 hours
  3. temperatureCool
  4. customthe reaction
  5. washwash with water
  6. dry with materialDry the organic layer (Na2SO4)
  7. customremove the solvent in vacuo
  8. customto afford crude product
  9. custompurify on silica with a 50 to 75% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-c65aac406fc943e28ad45bcc4ad03401
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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