1-Hydroxybenzotriazole → tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamate

HRID 660386Notes

Reaction equation

HRID 660386 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:27])[C@@H:4]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:5][C@H:6]([CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:7]([CH3:9])[CH3:8].[CH3:28][C:29]([CH3:37])([CH2:33][CH2:34][CH2:35][CH3:36])[C:30](O)=[O:31].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:12]([O:11][CH2:10][C@H:6]([CH:7]([CH3:9])[CH3:8])[CH2:5][C@H:4]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C@@H:3]([OH:27])[CH2:2][NH:1][C:30](=[O:31])[C:29]([CH3:37])([CH3:28])[CH2:33][CH2:34][CH2:35][CH3:36])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1632172,2-Dimethylhexanoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59630993tert-butyl (2S,3S,5S)-1-amino-5-(benzyloxymethyl)-2-hydroxy-6-methylheptan-3-ylcarbamate

Product 1

HCID 59630981tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamateYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (2S,3S,5S)-1-amino-5-(benzyloxymethyl)-2-hydroxy-6-methylheptan-3-ylcarbamate (500 mg, 1.32 mmol) in CH2Cl2 (15 mL), were added 2,2-dimethylhexanoic acid (220 mg, 1.45 mmol), HOBt (360 mg, 2.65 mmol) and EDCl (500 mg, 2.65 mmol). The mixture was cooled to 0° C. and DIEA (850 mg, 6.6 mmol) was added. The resulting mixture was allowed to warm to rt and stirred for 5 h. The reaction mixture was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo to give crude product, which was purified by column chromatography on silica gel to produce tert-butyl (2S,3S,5S)-5-(benzyloxymethyl)-1-(2,2-dimethylhexanamido)-2-hydroxy-6-methylheptan-3-ylcarbamate (310 mg, 46%); MS: 507 (M++1)

Workup

  1. temperatureto warm to rt
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give crude product, which
  7. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2534ae6c9ac54e4c8f9cd47571acc3e9
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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