Triethylamine → HCID 86642100, compound

HRID 1943184Notes

Reaction equation

HRID 1943184 reaction equation
[OH:1][CH2:2][C@H:3]1[N:13]2[C:14]3[N:5]([C:6](=[O:26])[CH2:7][N:8]([C:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:17])[C:9]=3[CH:10]=[CH:11][C:12]2=[O:15])[CH2:4]1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[CH3:34][S:35]([O:1][CH2:2][C@H:3]1[N:13]2[C:14]3[N:5]([C:6](=[O:26])[CH2:7][N:8]([C:16]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:17])[C:9]=3[CH:10]=[CH:11][C:12]2=[O:15])[CH2:4]1)(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58001795HCID 58001795, compound

Product 1

HCID 86642100HCID 86642100, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenylmethyl (1S)-1-(hydroxymethyl)-3,8-dioxo-1,2,3,4-tetrahydro-5H,8H-2a,5,8a-triazaacenaphthylene-5-carboxylate (242 mg, 0.681 mmol) (for a preparation see Example 13(g)) was dissolved in DCM (10 ml) at room temperature under argon and then treated with triethylamine (0.114 ml, 0.817 mmol). The mixture was then cooled using an ice-water bath. Methanesulfonyl chloride (0.058 ml, 0.749 mmol) was then added and the reaction was allowed to warm up to room temperature. After 1 h the mixture was washed with sat NaHCO3 (10 ml). The aqueous layer was extracted with DCM (2×50 ml) and the combined organic extracts dried on MgSO4, filtered and evaporated to afford the product as a yellow foam (232 mg, 95% purity by LCMS, 74.7%).

Workup

  1. temperatureThe mixture was then cooled
  2. washAfter 1 h the mixture was washed with sat NaHCO3 (10 ml)
  3. extractionThe aqueous layer was extracted with DCM (2×50 ml)
  4. customthe combined organic extracts dried on MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-31dd74d6b9b145c4ae4a7a1a54060765
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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