Ethanol → HCID 58828620, compound

HRID 1711395Notes

Reaction equation

HRID 1711395 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]([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:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.O.O.[Sn](Cl)Cl.O>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([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:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 61436Stannous chloride dihydrateHCID 588286253-[3-(Naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 58828620HCID 58828620, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 3-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-pyrrolidine-1-carboxylic acid benzyl ester (3.1 g, 5.7 mmol) in ethyl acetate was treated sequentially with ethanol and tin (II) chloride dihydrate (20.2 g, 89.5 mmol), stirred at 75° C., under nitrogen, for 2 hours, 20 minutes, poured into excess water and extracted with ethyl acetate. The combined extracts were washed sequentially with 2.5 N sodium hydroxide and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo for 20 minutes at 80° C. to yield 3-[4-amino-3-(naphthalene-1-sulfonylmethyl)-phenoxy]-pyrrolidine-1-carboxylic acid benzyl ester as a yellow solid, 2.37 g (82% yield), mp 162-4° C.; Mass spectrum (+EI, [M+H]+) m/z 517. 1HNMR (500 MHz, DMSO-d6): δ8.60-8.63 (m, 1H), 8.26 (dd, 1H, J=12.81 Hz and 8.23 Hz), 8.03-8.08 (m, 2H), 7.58-7.72 (m, 3H), 7.27-7.40 (m, 5H), 6.56-6.61 (m, 2H), 6.06 (s, 1H), 5.03-5.09 (m, 2H), 4.72 (s, 2H), 4.67 (s, 2H), 4.30 (s, 1H), 3.32-3.42 (m, 2H), 3.15-3.21 (m, 2H), 1.74-1.81 (m, 1H), 1.66-1.63 ppm (m, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed sequentially with 2.5 N sodium hydroxide and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo for 20 minutes at 80° C.

Sources & evidence

ORD record
ord-a3461b89fb83480195d439d406b856a3
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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