Azidotrimethylsilane → HCID 46179902, compound

HRID 73129Notes

Reaction equation

HRID 73129 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8](=[O:16])[C@H:9]([NH:12][C:13](=[O:15])[CH3:14])[CH2:10][OH:11])=[CH:4][CH:3]=1.[Si]([N:23]=[N+:24]=[N-])(C)(C)C>CC#N>[N:1]([C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8](=[O:16])[C@H:9]([NH:12][C:13](=[O:15])[CH3:14])[CH2:10][OH:11])=[CH:17][CH:18]=1)=[N+:23]=[N-:24]

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 46179901HCID 46179901, compound

Product 1

HCID 46179902HCID 46179902, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a cooled (0° C.) CH3CN solution (70 mL) of (R)—N-(4-aminobenzyl)-2-acetamido-3-hydroxypropanamide (2.40 g, 9.56 mmol) maintained under Ar, t-BuONO (3.41 mL, 28.68 mmol) followed by TMSN3 (3.02 mL, 22.94 mmol) were slowly added. The resulting solution was allowed to stir at room temperature (16 h) under Ar. The solvent was removed in vacuo, and the product was purified by column chromatography (SiO2; 1/9 MeOH/CHCl3) to give 2.10 g (79%) of (R)—N-(4-azidobenzyl)-2-acetamido-3-hydroxypropanamide as a white solid: mp 161-163° C.; [α]26D +13.2° (c 1.0, MeOH); Rf=0.35 (1/9 MeOH/CHCl3); IR (nujol mull) 3268, 2924, 2128, 1649, 1553, 1459 cm−1; 1H NMR (DMSO-d6) δ 1.87 (s, CH3C(O)), 3.58 (t, J=5.7 Hz, CH2OH), 4.26-4.32 (m, CH2Ar and CH), 4.91 (t, J=5.7 Hz, OH), 7.03-7.08 (m, 2 ArH), 7.28-7.31 (m, 2 ArH), 7.94 (d, J=8.1 Hz, NHCH), 8.40 (1, J=6.0 Hz, NHCH2); 13C NMR (DMSO-d6) δ 22.7 (CH3C(O)), 41.5 (CH2Ph), 55.3 (CH), 61.7 (CH2OH), 118.9, 128.7, 136.5, 137.7 (C6H5), 169.4, 170.3 (2C(O)); HRMS (ESI) 278.1249 [M+H+] (calcd. for C12H16N6O3 278.1253); Anal. (C12H15N5O3) Calcd.: C, 51.98%; H, 5.45%; N, 25.26%. Found: C, 51.93%; H, 5.47%; N, 24.98%.

Workup

  1. temperaturemaintained under Ar
  2. additionwere slowly added
  3. customThe solvent was removed in vacuo
  4. customthe product was purified by column chromatography (SiO2; 1/9 MeOH/CHCl3)

Sources & evidence

ORD record
ord-2aebf6a95f8a4084a762b19ab0cf6c05
Source dataset
uspto-grants-2014_09
Patent number
US08829033B2

Reaction notes

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