Diisopropylethylamine → [(4-Cyclopropylmethoxy-benzenesulfonyl)-(4-dimethylamino-benzyl)-amino]-acetic acid methyl ester

HRID 2216653Notes

Reaction equation

HRID 2216653 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1.C(N(C(C)C)CC)(C)C.[CH:26]1([CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=2)[CH2:28][CH2:27]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]([S:37]([C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:29][CH:26]2[CH2:27][CH2:28]2)=[CH:36][CH:35]=1)(=[O:39])=[O:38])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]([CH3:15])[CH3:14])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 113686084-(cyclopropylmethoxy)benzenesulfonyl ChlorideHCID 11401797(4-Dimethylamino-benzylamino)-acetic acid methyl ester

Product 1

HCID 11224248[(4-Cyclopropylmethoxy-benzenesulfonyl)-(4-dimethylamino-benzyl)-amino]-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 49.4 g (222 mmol) of [(4-dimethylamino-benzylamino)-acetic acid methyl ester], 41.4 ml (244 mmol) of diisopropylethyl amine and 0.271 g (2.2 mmol) of DMAP in 600 ml of CH2Cl2, 54.8 g (222 mmol) of 4-cyclopropylmethoxy-benzenesulfonyl chloride in 100 ml of CH2Cl2 are added at 0–5° C. After stirring for 15 h at r.t., the reaction mixture is quenched with ice water and sat. aqueous NH4CO3. The mixture is extracted with AcOEt and combined extracts are washed with sat. aqueous NH4CO3 and brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by CC on silica gel (n-Hexane: AcOEt=4:1) to give the title compound as a colorless solid.

Workup

  1. customthe reaction mixture is quenched with ice water and sat. aqueous NH4CO3
  2. extractionThe mixture is extracted with AcOEt and combined extracts
  3. washare washed with sat. aqueous NH4CO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by CC on silica gel (n-Hexane: AcOEt=4:1)

Sources & evidence

ORD record
ord-9ecdc24a332b4e76800d0a54d2160c0c
Source dataset
uspto-grants-2006_09
Patent number
US07112611B2

Reaction notes

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