Hydroxyamine hydrochloride → HCID 71073681, compound

HRID 2405198Notes

Reaction equation

HRID 2405198 reaction equation
[C:1]([O:5][C:6](=[O:32])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:31])[C:13](=C(C1C=CC=CC=1)C1C=CC=CC=1)[NH:14][NH:15][C:16]#[CH:17])([CH3:4])([CH3:3])[CH3:2].Cl.NO>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:32])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:31])[CH2:13][NH:14][NH:15][C:16]#[CH:17])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86674306HCID 86674306, compound

Product 1

HCID 71073681HCID 71073681, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

As reported for the synthesis of 19b in reference 46, benzhydrylidene aza-propargylglycinyl-proline tert-butyl ester 18a (100 mg, 0.23 mmol) was stirred with hydroxylamine hydrochloride (29 mg, 0.42 mmol) in 20 mL of pyridine overnight at 60° C. The volatiles were removed by rotary evaporation followed by co-evaporation with dichloromethane and ethyl acetate until solidification. Purification by flash chromatography on silica gel using a 1:1 mixture of ethyl acetate in hexane afforded amine 19a (51.3 mg, 84%) as a pale yellow foam: Rf=0.39 (hexane/EtOAc 1:1); [α]20D −48° (c 1.15, CHCl3). 1H NMR (CDCl3, 400 MHz) δ 1.46 (s, 9H), 1.84-1.99 (m, 3H), 2.13-2.20 (m, 1H), 2.31 (s, 1H), 3.64 (m, 2H), 4.16 (d, J=17.2 Hz, 1H), 4.24 (d, J=17.2 Hz, 1H), 4.43 (m, 1H); 13C NMR (CDCl3, 100 MHz) δ23.3, 27.6, 30.1, 42.6, 48.8, 61.5, 73.0, 78.1, 80.3, 159.8, 172.5. HRMS m/z calculated for C13H21N3O3 Na [M+Na]+ 290.1475. found 290.1488.

Workup

  1. customThe volatiles were removed by rotary evaporation
  2. customPurification by flash chromatography on silica gel using
  3. additiona 1:1 mixture of ethyl acetate in hexane

Sources & evidence

ORD record
ord-8ed1b183b6844ee4b0d2a08acf5f942d
Source dataset
uspto-grants-2014_08
Patent number
US08802818B2

Reaction notes

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