4-Toluenesulfonyl chloride → HCID 86611756, compound

HRID 1716584Notes

Reaction equation

HRID 1716584 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH2:13][C@H:12]([CH2:17][OH:18])[CH2:11]2)([CH3:4])([CH3:3])[CH3:2].[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([NH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH2:13][C@H:12]([CH2:17][O:18][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27])[CH2:11]2)=[O:19])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68511182HCID 68511182, compound

Product 1

HCID 86611756HCID 86611756, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The aforementioned (S)-2-hydroxymethyl-indan-5-yl-carbamic acid tert-butyl ester (2.15 g, 8.16 mmol) was dissolved in 50 mL of CH2Cl2. p-Toluenesulfonyl chloride (1.63 g, 8.54 mmol) and DMAP (1.1 g, 9.0 mmol) were added and the solution was stirred for 22 hours at rt. The reaction mixture was diluted with 50 mL of CH2Cl2 and washed in turn with saturated aqueous NH4Cl, saturated aqueous NaHCO3 and brine (100 mL each). Each wash was extracted with a small portion of CH2Cl2. The extracts were combined, dried over Na2SO4, filtered and evaporated. The residue was dissolved in warm ethyl ether (25 mL) and allowed to crystallize. The solid was filtered, washed with cold ethyl ether and dried to provide a beige solid as toluene-4-sulfonic acid (S)-5-tert-butoxycarbonylamino-indan-2-ylmethyl ester (2.1 g, 86%). 1H-NMR and MS data were compatible with the structure.

Workup

  1. washwashed in turn with saturated aqueous NH4Cl, saturated aqueous NaHCO3 and brine (100 mL each)
  2. extractionEach wash was extracted with a small portion of CH2Cl2
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue was dissolved in warm ethyl ether (25 mL)
  7. customto crystallize
  8. filtrationThe solid was filtered
  9. washwashed with cold ethyl ether
  10. customdried

Sources & evidence

ORD record
ord-7b31d3553b854c0f85442ac81a6aa32e
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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