Tetrahydrofuran → HCID 18704405, compound

HRID 2287281Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].C([N:14]([CH2:17][CH3:18])CC)C.O1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH2:5]([O:4][C:2]([NH:14][CH:17]([CH2:18][CH2:20][CH2:21][CH2:22][CH2:23][CH2:10][CH2:11][CH2:6][CH2:7][CH2:8][CH2:9][CH2:23][CH2:22][CH2:21][CH3:20])[C:2]([OH:4])=[O:3])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 10387Benzyl chloroformate

Product 1

HCID 18704405HCID 18704405, compound

Procedure

6.82 g (40 mmol) of benzyl chloroformate (Z--Cl) is added in drops to 10 g (35.03 mmol) of the title compound of Example 19a and 8.86 g (87.57 mmol) of triethylamine in 200 ml of tetrahydrofuran at 0° C. It is stirred for 5 hours at 0° C. It is evaporated to the dry state in a vacuum, the residue is taken up in 300 ml of dichloromethane and washed twice with 200 ml of 5% aqueous hydrochloric acid each. The organic phase is dried on magnesium sulfate and evaporated to the dry state. The residue is recrystallized from diisopropyl ether.

Sources & evidence

ORD record: ord-44851769b18d4d218e3233e140b57b2a
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06083479

Reaction notes

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