Phosphorus sulfide (P2S5) → HCID 86634824, compound

HRID 1808142Notes

Reaction equation

HRID 1808142 reaction equation
[C:1](=[O:22])([O:3][C@H:4]([CH:8]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[C:5]([NH2:7])=O)[NH2:2].C(=O)([O-])O.[Na+].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:29]>C(COC)OC>[C:1](=[O:22])([O:3][C@H:4]([CH:8]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[C:5]([NH2:7])=[S:29])[NH2:2]

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 68920845HCID 68920845, compound

Product 1

HCID 86634824HCID 86634824, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (R)-tert-butyl-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl carbamate (6.80 g, 22.4 mmol) in anhydrous dimethoxyethane (100 mL) was mixed in portions with sodium hydrogencarbonate (7.14 g, 85.1 mmol) and diphosphorus pentasulphide (10.2 g, 44.8 mmol) and stirred overnight at room temperature. The reaction mixture was concentrated to low volume in a vacuum, the residue taken up in ethyl acetate (100 mL) and washed with water and saturated sodium hydrogencarbonate solution (3×50 mL each). The organic phase was dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product was taken up in diethyl ether/cyclohexane (50 mL each) and concentrated to low volume again. During this, the product separated out as a white solid, which was filtered off.

Workup

  1. concentrationThe reaction mixture was concentrated to low volume in a vacuum
  2. washwashed with water and saturated sodium hydrogencarbonate solution (3×50 mL each)
  3. dry with materialThe organic phase was dried with sodium sulphate
  4. concentrationconcentrated to low volume in a vacuum
  5. concentrationconcentrated to low volume again
  6. customDuring this, the product separated out as a white solid, which
  7. filtrationwas filtered off

Sources & evidence

ORD record
ord-a258d4df75f04482b225b5e48cfb26de
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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