(R)-3-Pyrrolidinol → HCID 9956740, compound

HRID 379573Notes

Reaction equation

HRID 379573 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.[CH3:7][N:8]1[C:13](=[O:14])[C:12]2[C:15]([S:25](Cl)(=[O:27])=[O:26])=[C:16]([CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[S:17][C:11]=2[N:10]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:9]1=[O:33]>>[CH3:7][N:8]1[C:13](=[O:14])[C:12]2[C:15]([S:25]([N:4]3[CH2:5][CH2:6][C@@H:2]([OH:1])[CH2:3]3)(=[O:27])=[O:26])=[C:16]([CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[S:17][C:11]=2[N:10]([CH2:29][CH:30]([CH3:31])[CH3:32])[C:9]1=[O:33]

Participants

3

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 18366603HCID 18366603, compound

Product 1

HCID 9956740HCID 9956740, compound

Procedure

(R)-3-Hydroxypyrrolidine (50 mg) was added to the solution of 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-6-(3-pyrdinyl)methyl-2,4-dioxothieno[2,3-d]pyrimidine-5-sulfonyl chloride (20 ml). After 1 hour, the solution was dried over anhydrous magnesium sulfate and filtered through a small silica pad, washing with ethyl acetate/methanol (19:1). The filtrate was evaporated and the residue was purified by preparative HPLC with dichloromethane:ethanol gradient elution followed by crystallisation from ethyl acetate/isohexane to give the title compound (11 mg).

Workup

  1. dry with materialthe solution was dried over anhydrous magnesium sulfate
  2. filtrationfiltered through a small silica pad
  3. washwashing with ethyl acetate/methanol (19:1)
  4. customThe filtrate was evaporated
  5. customthe residue was purified by preparative HPLC with dichloromethane
  6. washethanol gradient elution
  7. customfollowed by crystallisation from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-d720b586eafb4645bfbf33656a8667fc
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

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