HCID 59680788, compound → HCID 10840267, compound

HRID 1394000Notes

Reaction equation

HRID 1394000 reaction equation
C([O:10][C:11](=[O:48])[C@H:12]([C@@H:21]([CH3:47])[O:22][C:23](=[O:46])[C@H:24]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)[N:25]([C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[CH3:26])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])C(C1C=CC=CC=1)=O>CC(O)=O.[Zn]>[CH2:30]([O:29][C:27]([N:25]([CH3:26])[C@H:24]([C:23]([O:22][C@H:21]([CH3:47])[C@@H:12]([C:11]([OH:48])=[O:10])[NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])=[O:46])[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)=[O:28])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 1

HCID 59680788HCID 59680788, compound

Product 1

HCID 10840267HCID 10840267, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a homogeneous solution of D2 (24.49 g, 38.4 mmol) in aq AcOH (211 ml, 90%) at 0° C., powdered Zn was added (18.65 g, 288.3 mmol). The resulting mixture was stirred at 0° C. for 3 h until disappearance of the starting material (followed by TLC), The reaction mixture was filtered over celite and washing with EtOAc (200 ml). The filtrate was concentrated at reduced pressure and the residue was chased with Et2O (200 ml) and filtered. The filtrate was successively partitioned between aq KHSO4(100 ml, 10%) and brine (100 ml). The organic phase was dried (Na2SO4) and concentrated to give an oil which was purified by flash LC (Lichroprep RPC18, ACN:H2O 1:1 (800 ml, then 7.3 (600 ml)] to yield D1 (15.53 g, 74%) as a white solid. [α]D24 −27.6 (c 2.187, DCM); lit [α]D −20.5 (c 2, DCM), JOC, 62, 2, 1997. Rf=0.58 [ACN/H2O (7:3)].

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. washwashing with EtOAc (200 ml)
  3. concentrationThe filtrate was concentrated at reduced pressure
  4. filtrationfiltered
  5. customThe filtrate was successively partitioned between aq KHSO4(100 ml, 10%) and brine (100 ml)
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. concentrationconcentrated
  8. customto give an oil which
  9. customwas purified by flash LC (Lichroprep RPC18, ACN:H2O 1:1 (800 ml

Sources & evidence

ORD record
ord-8bd64eca0c724157917b89b32187c2f0
Source dataset
uspto-grants-2008_03
Patent number
US07348310B2

Reaction notes

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