Acetyl chloride → HCID 131723573, compound

HRID 992460Notes

Reaction equation

HRID 992460 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].Cl.[CH2:6]([O:13][C@H:14]1[CH2:18][NH:17][C@H:16]([C:19]([OH:21])=[O:20])[CH2:15]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:22](N(CC)CC)C>N1C=CC=CC=1>[N:17]1([C:1]([CH3:2])=[O:3])[CH2:18][C@H:14]([O:13][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:15][C@H:16]1[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 56777261(4R)-4-(Benzyloxy)-L-proline--hydrogen chloride (1/1)

Product 1

HCID 131723573HCID 131723573, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride (3.3 mL, 46 mmol) was added dropwise to a solution of trans-4-benzyloxy-L-proline hydrochloride (H-Hyp(OBzl)-OMe.HCl; 12.5 g, 46 mmol), triethylamine (6.4 mL, 46 mmol) in pyridine (150 mL) at 0° C. while stirring under argon. The reaction mixture was stirred for 30 min at 0° C. then slowly warmed to room temperature over 16 h. The reaction mixture was concentrated in vacuo, diluted with CH2Cl2, washed with 1 N aqueous HCl (3×), 10% aqueous Na2CO3, saturated aqueous NaHCO3, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with ethyl acetate/hexane (3:2) to give Ac-Hyp(OBzl)-OMe as an oil.

Workup

  1. stirringThe reaction mixture was stirred for 30 min at 0° C.
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with CH2Cl2
  4. washwashed with 1 N aqueous HCl (3×), 10% aqueous Na2CO3, saturated aqueous NaHCO3, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate/hexane (3:2)

Sources & evidence

ORD record
ord-7922e54eba774e54aefff081f8ad0699
Source dataset
uspto-grants-2002_10
Patent number
US06469036B1

Reaction notes

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