Trityl chloride → HCID 57106768, compound

HRID 325006Notes

Reaction equation

HRID 325006 reaction equation
[NH2:1][C@H:2]1[C@H:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[NH:4][C:3]1=[O:14].[C:15]1([C:21](Cl)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C>ClCCl.O>[CH3:13][O:12][C:10]([CH2:9][CH2:8][CH2:7][O:6][C@@H:5]1[NH:4][C:3](=[O:14])[C@H:2]1[NH:1][C:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:11]

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 57266910HCID 57266910, compound

Product 1

HCID 57106768HCID 57106768, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(3S,4S)-3-Amino-4-[3-(methoxycarbonyl)propoxy]azetidin-2-one (30 mg, 0.148 mmol) was dissolved in dry dichloromethane (2 mL) and treated with triphenylmethyl chloride (41 mg, 0.148 mmol) followed by diisopropylethylamine (19 mg, 0.148 mmol). The solution was stirred at RT under argon for 5 h, diluted with water and extracted with dichloromethane. The organic phases were combined, washed with water and brine, dried (magnesium sulfate), filtered, and concentrated. The residue was purified by preparative thin layer chromatography (Whatman, silica gel 60A, 20×20 cm, 1000 um, 40% ethyl acetate:hexane) to give the title compound (7 mg). MS(ES) m/e 445.2 [M+H].

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative thin layer chromatography (Whatman, silica gel 60A, 20×20 cm, 1000 um, 40% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-095fd577574c434c9543f3eb2d3cab1d
Source dataset
uspto-grants-2001_04
Patent number
US06221860B1

Reaction notes

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