p-Toluenesulfonic acid monohydrate → HCID 12112498, compound

HRID 1243283Notes

Reaction equation

HRID 1243283 reaction equation
[C:1]([O:5][C:6](=[O:40])[NH:7][C@@H:8]([CH2:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([F:39])[CH:33]=1)[C@@H:9]([OH:30])[CH2:10][C@H:11]([C:14](N1[C@H]2C3C=CC=CC=3C[C@H]2OC1(C)C)=[O:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:40])[NH:7][C@H:8]([C@@H:9]1[CH2:10][C@@H:11]([CH2:12][CH3:13])[C:14](=[O:15])[O:30]1)[CH2:31][C:32]1[CH:33]=[C:34]([F:39])[CH:35]=[C:36]([F:38])[CH:37]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12988679HCID 12988679, compound

Product 1

HCID 12112498HCID 12112498, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(1S,2S,4R)-[1-(3,5-Difluorobenzyl)-4-((3aS,8aR)-2,2-dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazole-3-carbonyl)-2-hydroxyhexyl]-carbamic acid tert-butyl ester (VIII, 60 mg) was dissolved in 5:1 toluene/CH2C12 (3 mL), and p-toluenesulfonic acid monohydrate (23 mg) was added. This was stirred at rt for 18 h. The mixture was then filtered, and partitioned between half-saturated NaHCO3 (3 mL) and 1:1 EtOAc/hexanes (2×3 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. Flash chromatography of the residue afforded desired product as a solid: MH+370.2.

Workup

  1. additionwas added
  2. filtrationThe mixture was then filtered
  3. custompartitioned between half-saturated NaHCO3 (3 mL) and 1:1 EtOAc/hexanes (2×3 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-771bcd866a1a470599a47d377b6f5b3e
Source dataset
uspto-grants-2006_10
Patent number
US07119085B2

Reaction notes

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