Diethyl Ether → HCID 86700113, compound

HRID 1755469Notes

Reaction equation

HRID 1755469 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:34])[C@@H:14]([NH:16][C:17](=[O:33])[C@@H:18]([NH:20][C:21](=[O:32])[C@@H:22]([NH:24]C(=O)OC(C)(C)C)[CH3:23])[CH3:19])[CH3:15])=[N:5][CH:4]=1)=[O:2].CCOCC>O1CCOCC1.Cl>[NH2:24][C@@H:22]([CH3:23])[C:21]([NH:20][C@@H:18]([CH3:19])[C:17]([NH:16][C@@H:14]([CH3:15])[C:13]([NH:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]1[S:7][C:3]([CH:1]=[O:2])=[CH:4][N:5]=1)=[O:34])=[O:33])=[O:32]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 86700114HCID 86700114, compound

Product 1

HCID 86700113HCID 86700113, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of material from Example 73 (213 mg, 0.427 mmol) in Dioxane (10 mL), is added HCl, 4.0M in dioxane (92 mL, 368 mmol) and HCl, 1.0M in Et2O (10.4 mL, 10.4 mmol). The resulting suspension is stirred at room temp 4 h and then the solvent is evaporated off under a gentle stream of N2. The resulting residue is suspended in CH2Cl2 (60 mL) and the solvent is removed in vacuo (repeat 4 times) to give the title compound (quantitative yield) as an off white solid, as an HCl salt. LC/MS (Condition A): ret. T=1.35 min, (M+H)+ 399.20.

Workup

  1. customthe solvent is evaporated off under a gentle stream of N2
  2. customthe solvent is removed in vacuo (repeat 4 times)

Sources & evidence

ORD record
ord-de4969ba08484bea95cebcdc19b829cb
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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