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2-Naphthalenesulfonyl chloride → (R)-3-(Naphthalene-2-sulfonamido)-3-phenylpropanoic Acid

HRID 32047
Notes
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Reaction equation

HRID 32047 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11](Cl)(=[O:13])=[O:12].[OH-].[Na+].Cl.[NH2:18][C@@H:19]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:20][C:21]([OH:23])=[O:22].CN1CCOCC1>O1CCOCC1.C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:18][C@@H:19]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:20][C:21]([OH:23])=[O:22])(=[O:13])=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 71252-Naphthalenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 14798Sodium Hydroxide2×HCID 2734697(3R)-3-amino-3-phenylpropanoic acid hydrochloride

Product 1

HCID 7549440(R)-3-(Naphthalene-2-sulfonamido)-3-phenylpropanoic Acid

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

Naphthalene-2-sulfonyl chloride (18.18 g, 80.2 mmol) and NaOH (60 mL, 2 N) were added portion-wise over 1 h to a mixture of (R)-3-amino-3-phenyl-propionic acid HCl salt (14.70 g, 72.9 mmol) and N-methylmorpholine (4.0 mL, 36.5 mmol) in dioxane (250 mL). The pH was maintained at pH 11 with the 2N NaOH solution during the addition. After stirring for an additional 3 h, the mixture was diluted with CH2Cl2 (1 L), acidified, washed with water, dried over MgSO4, filtered, and concentrated in vacuo. Crystallization from CH2Cl2/hexane furnished the title compound. MS (-ESI, m/z) 354 (M−H)−.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customCrystallization from CH2Cl2/hexane

Sources & evidence

ORD record
ord-1f9777ffa2b84502bae8709b156652e9
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425631B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes