Chloroacetyl chloride → trans-N-benzyl-2-chloro-N-(4-hydroxytetrahydrofuran-3-yl)acetamide

HRID 1852773Notes

Reaction equation

HRID 1852773 reaction equation
[CH2:1]([NH:8][C@@H:9]1[CH2:13][O:12][CH2:11][C@H:10]1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)Cl>[CH2:1]([N:8]([C@H:9]1[C@H:10]([OH:14])[CH2:11][O:12][CH2:13]1)[C:24](=[O:25])[CH2:23][Cl:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 86724519trans-4-(Benzylamino)tetrahydrofuran-3-ol

Product 1

HCID 86724520trans-N-benzyl-2-chloro-N-(4-hydroxytetrahydrofuran-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of trans-4-(benzylamino)tetrahydrofuran-3-ol (4.1 g, 21.2 mmol) in CH2Cl2 (40 mL) at −40° C. was added triethylamine (5.9 mL, 42.4 mmol) followed by dropwise addition of 2-chloroacetyl chloride (1.6 mL, 21.2 mmol). The reaction was stirred at −40° C. for 2 hours. The reaction was quenched with saturated aqueous NaHCO3 (40 mL) and extracted using CH2Cl2 (100 mL). The organic layer was separated, washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification of the residue on a silica gel column with 0 to 100% EtOAc/hexanes afforded trans-N-benzyl-2-chloro-N-(4-hydroxytetrahydrofuran-3-yl)acetamide. MS APCI calc'd for C13H16ClNO3 [M+H]+ 270. found 270.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 (40 mL)
  2. extractionextracted
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue on a silica gel column with 0 to 100% EtOAc/hexanes

Sources & evidence

ORD record
ord-67c43bc16de744e5b4f2cf7f58a20ccf
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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