Chloroacetaldehyde → HCID 59178949, compound

HRID 1947672Notes

Reaction equation

HRID 1947672 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([NH2:28])=[S:27])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29][C:30](OC(C)=O)=O.ClCC=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:15][CH2:16][N:17]([C:20]3[CH:21]=[CH:22][C:23]([C:26]4[S:27][CH:29]=[CH:30][N:28]=4)=[CH:24][CH:25]=3)[CH2:18][CH2:19]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 7918Acetic AnhydrideHCID 59178921HCID 59178921, compound

Product 1

HCID 59178949HCID 59178949, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of the product of Example 12.24, Step 1 above (151 mg; 0.374 mmol) in DMF (3 ml) was treated with Ac2O (1 ml) and chloroacetaldehyde (587 mg; 50% aq. solution; 3.74 mmol). The solution was stirred at 80° C. for 1 hr. The reaction was partitioned between iPrOAc (50 mL) and aq. sodium bicarbonate (20 mL). The organic was washed three more times with aq. sodium bicarbonate (3×10 mL). The organic was dried over magnesium sulfate, filtered and evaporated to a brown semi-solid. The solid was digested (refluxing MTBE). The nearly homogenous solution was allowed to stand at −10° C. for 1 hr, causing the deposition of a tan solid. The supernatant was drawn off and the solid rinsed with MTBE. All volatiles were removed and light tan solid was chromatographed (PTLC; 40:1 CH2Cl2/MeOH), affording the title compound.

Workup

  1. customThe reaction was partitioned between iPrOAc (50 mL) and aq. sodium bicarbonate (20 mL)
  2. washThe organic was washed three more times with aq. sodium bicarbonate (3×10 mL)
  3. dry with materialThe organic was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to a brown semi-solid
  6. temperature(refluxing MTBE)
  7. waitto stand at −10° C. for 1 hr
  8. washthe solid rinsed with MTBE
  9. customAll volatiles were removed
  10. customlight tan solid was chromatographed (PTLC; 40:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-7269bbce02d942dd9adf1089f169bd16
Source dataset
uspto-grants-2013_03
Patent number
US08399485B2

Reaction notes

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