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Diisopropylethylamine → N-[5-((1R)-2-{[6-({4-[3-(cyclopentylsulfonyl)phenyl]butyl}oxy)hexyl]amino}-1-hydroxyethyl)-2-hydroxyphenyl]methanesulfonamide

HRID 2118349
Notes
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Reaction equation

HRID 2118349 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)[OH:4].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([S:35]([CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)(=[O:37])=[O:36])[CH:30]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:38]1([S:35]([C:31]2[CH:30]=[C:29]([CH2:28][CH2:27][CH2:26][CH2:25][O:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH:1][CH2:2][C@@H:3]([C:5]3[CH:6]=[CH:7][C:8]([OH:16])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=3)[OH:4])[CH:34]=[CH:33][CH:32]=2)(=[O:37])=[O:36])[CH2:42][CH2:41][CH2:40][CH2:39]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 691198271-{4-[(6-Bromohexyl)oxy]butyl}-3-(cyclopentylsulfonyl)benzene

Product 1

HCID 69119709N-[5-((1R)-2-{[6-({4-[3-(cyclopentylsulfonyl)phenyl]butyl}oxy)hexyl]amino}-1-hydroxyethyl)-2-hydroxyphenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

N-{5-[(1R)-2-Amino-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide (33.2 mg) was added to a solution of 1-{4-[(6-bromohexyl)oxy]butyl}-3-(cyclopentylsulfonyl)benzene (Example 1v.) (50 mg) in DMF (5 ml). The reaction mixture was treated with N,N-diisopropylethylamine (29.3 μl) and stirred at room temperature for 113 h. The reaction mixture was partitioned between EtOAc and water and the organic extracts were washed with ammonium chloride, dried (MgSO4) and concentrated in vacuo. The residue was purified by column DCM) to afford the title compound. LCMS RT=2.73 min 610(M+H)+

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washthe organic extracts were washed with ammonium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column DCM)

Sources & evidence

ORD record
ord-836c6e81763543239f90f9f722991fc2
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07442839B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes