Triethylamine → HCID 66728007, compound

HRID 879971Notes

Reaction equation

HRID 879971 reaction equation
[C:1]1([C:7]([NH:20][C@@H:21]([CH2:24][NH2:25])[CH2:22][OH:23])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[O:33]([C:40]1[CH:45]=[CH:44][C:43]([S:46](Cl)(=[O:48])=[O:47])=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[O:33]([C:40]1[CH:45]=[CH:44][C:43]([S:46]([NH:25][CH2:24][C@H:21]([NH:20][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:22][OH:23])(=[O:48])=[O:47])=[CH:42][CH:41]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27947564-Phenoxybenzene-1-sulfonyl chlorideHCID 10806499HCID 10806499, compound

Product 1

HCID 66728007HCID 66728007, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-triphenylmethylamino-3-aminopropanol (1.99 g, 6 mmol) in CH2Cl2 (12 mL) at 0° C., triethylamine (1.7 mL, 12 mmol) was added dropwise followed by the addition of 4-phenoxybenzenesulfonyl chloride (1.61 g in 12 mL CH2Cl2). The reaction mixture was stirred at RT for 2 h and then was washed with water (20 mL) and brine (20 mL). The organic layer was dried over anhydrous Na2SO4, concentrated and purified through column chromatography (silica gel, 35% EtoAc in pet. ether) to afford (S)-3-(4-phenoxybenzenesulfonamido)-2-(tritylamino)propanol as colorless solid in 74% (2.52 g) yield.

Workup

  1. washwas washed with water (20 mL) and brine (20 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. custompurified through column chromatography (silica gel, 35% EtoAc in pet. ether)

Sources & evidence

ORD record
ord-3ae5d13296044e559dab1e8499c6c262
Source dataset
uspto-grants-2015_03
Patent number
US08993544B2

Reaction notes

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