Triethylamine → HCID 86761255, compound

HRID 253566

Reaction equation

HRID 253566 reaction equation
[C:1]([C:3]1[CH:29]=[CH:28][C:6]([CH2:7][NH:8][CH2:9][C@@H:10]([OH:27])[C@@H:11]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1)#[N:2].[C:30](ON1C(=O)CCC1=O)([O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:31].CCN(CC)CC>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:9][C@@H:10]([OH:27])[C@@H:11]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:23])[CH3:24])[CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:30]([O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:31])=[CH:28][CH:29]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 57786472tert-butyl (2S,3R)-4-(4-cyanobenzylamino)-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate

Product 1

HCID 86761255HCID 86761255, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (2S,3R)-4-(4-cyanobenzylamino)-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate (600 mg, 1.5 mmol) in CH2Cl2 (30 mL) was treated with Teoc-OSu (762 mg, 3.0 mmol, 2.0 equiv) and Et3N (304 mg, 3.0 mmol, 2.0 equiv). The mixture was allowed to stir overnight at rt. LC-MS analysis showed that all of the free amine had been consumed. The solution was washed with water, 1.0 M aq HCl, and brine, then over dried over Na2SO4, filtered and evaporated to leave tert-butyl (2S,3R)-4-(N-(4-cyanobenzyl)-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate. NMR analysis showed that the compound was of sufficient purity to use in the next step.

Workup

  1. customhad been consumed
  2. washThe solution was washed with water, 1.0 M aq HCl, and brine
  3. dry with materialover dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d89397fea7824675a62bd57ea32c1d75
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Linked notes

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