Phosphorus sulfide (P2S5) → HCID 87622202, compound

HRID 1808140Notes

Reaction equation

HRID 1808140 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]>COCCOC>[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 68925239HCID 68925239, compound

Product 1

HCID 87622202HCID 87622202, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (S)-tert-butyl-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-yl carbamate (500 mg, 1.6 mmol) in anhydrous 1,2-dimethoxyethane (10 mL) was mixed in portions with sodium hydrogencarbonate (520 mg, 6.2 mmol) and diphosphorus pentasulphide (730 mg, 3.2 mmol) and stirred overnight at room temperature. The reaction mixture was then concentrated to low volume in a vacuum, the residue taken up in ethyl acetate (30 mL) and washed with water and saturated sodium hydrogencarbonate solution (3×20 mL each). The organic phase was dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product (600 mg) was taken up in diethyl ether/cyclohexane (10 mL each) and concentrated to low volume again. During this a white solid separated out.

Workup

  1. concentrationThe reaction mixture was then concentrated to low volume in a vacuum
  2. washwashed with water and saturated sodium hydrogencarbonate solution (3×20 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 a white solid separated out

Sources & evidence

ORD record
ord-ec4a5983e59844e8b50735bc3ea3d7d5
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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