Chloroacetaldehyde → HCID 178523005, compound

HRID 1013002Notes

Reaction equation

HRID 1013002 reaction equation
[NH2:1][CH:2]([C:12]1[N:17]=[C:16]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:19])[C:15]([OH:29])=[C:14]([OH:30])[N:13]=1)[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[Cl:38][CH2:39][CH:40]=O.[BH3-]C#N.[Na+]>CO.C(O)(=O)C>[CH2:5]([O:4][CH2:3][CH:2]([C:12]1[N:17]=[C:16]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:19])[C:15]([OH:29])=[C:14]([OH:30])[N:13]=1)[NH:1][CH2:40][CH2:39][Cl:38])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 33ChloroacetaldehydeHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 178511399HCID 178511399, compound

Product 1

HCID 178523005HCID 178523005, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a stirred suspension of compound of Step 3 in dry trimethylortoformiate, triethylamine (1.3 eq.) and 1.1 eq. of α-chloroacetaldehyde (1.1 eq.) were added. The resulting solution was aged for 2 hours at room temperature, the solvent was removed by rotary evaporation to afford a residue that was dissolved in MeOH, treated with acetic acid (pH=5) and NaBH3CN (1.1 eq.). The mixture was stirred overnight at room temperature then the solvent was removed by rotary evaporation and the resulting residue was taken in dry toluene and concentrated. This material was used without any purification for the next step. MS (ES) C23H24ClFN4O4 requires 474. Found: 475.

Workup

  1. additionwere added
  2. customthe solvent was removed by rotary evaporation
  3. customto afford a residue that
  4. customthe solvent was removed by rotary evaporation
  5. concentrationconcentrated
  6. customThis material was used without any purification for the next step

Sources & evidence

ORD record
ord-457ef0f7d4d841bfb66de8aa126b8750
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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