Chloroacetyl chloride → HCID 118117773, compound

HRID 1747210Notes

Reaction equation

HRID 1747210 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C@H:7]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([I:17])[CH:12]=1)[CH2:8][OH:9].CCN(CC)CC>C1COCC1>[Cl:1][CH2:2][C:3]([NH:6][C@@H:7]([CH2:8][OH:9])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([I:17])[CH:12]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 118117637HCID 118117637, compound

Product 1

HCID 118117773HCID 118117773, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Chloroacetylchloride (1.05 mL, 13.1 mmol) was added dropwise to a 0° C. solution of (R)-2-amino-3-(3-iodo-phenyl)-propan-1-ol A-8 (3.03 g, 10.9 mmol) and Et3N (1.98 mL, 14.2 mmol) in THF (50 mL) under argon and the resulting suspension was warmed to RT and stirred for 30 min. The reaction mixture was cooled back to 0° C. before being quenched with water and concentrated in vacuo. The remaining aq. phase was extracted with EtOAc (2×) and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo to give the title compound as a cream solid that was used further without purification. LC-MS B: tR=0.71 min; [M(35Cl)+H]+=353.75.

Workup

  1. custombefore being quenched with water
  2. concentrationconcentrated in vacuo
  3. extractionThe remaining aq. phase was extracted with EtOAc (2×)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-8fa3064a717d4ce4baec3e6895e4e4f7
Source dataset
uspto-grants-2015_10
Patent number
US09150566B2

Reaction notes

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