Sodium Bicarbonate → HCID 178525139, compound

HRID 1711417Notes

Reaction equation

HRID 1711417 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[C:21]([CH2:26][S:27]([C:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH:33]=[CH:32][CH:31]=3)(=[O:29])=[O:28])[CH:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:40]([O-])=O.[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.Cl.O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][O:18][C:19]2[CH:20]=[C:21]3[C:22](=[CH:23][CH:24]=2)[NH:25][N:40]=[C:26]3[S:27]([C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][CH:31]=2)(=[O:29])=[O:28])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 588286244-[4-Amino-3-(1-naphthylsulfonylmethyl)phenoxymethyl]piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 178525139HCID 178525139, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[4-amino-3-(1-naphthylsulfonylmethyl)phenoxymethyl]-piperidine-1-carboxylic acid benzyl ester (0.74 g, 1.36 mmoles) in THF and 4M HCl (10 mL), under nitrogen, at 3° C. was treated dropwise with a solution of sodium nitrite (0.09 g, 1.42 mmoles) in H2O, poured into a cold solution of saturated sodium bicarbonate and extracted with EtOAc. The extracts were combined, dried over Na2SO4 and concentrated under vacuum to afford the title compound as an off white solid (0.71 g, 1.29 mmoles).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0330a31b9b3342278c51f036f2ba53cb
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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