Triphenylphosphine → CID 71511789

HRID 335490Notes

Reaction equation

HRID 335490 reaction equation
[CH2:1]([NH:3][C:4]1[S:5][C@H:6]2[O:12][C@H:11]([CH2:13]O)[C@@H:10]([OH:15])[C@H:9]([OH:16])[C@H:7]2[N:8]=1)[CH3:2].[Cl:17]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O>[Cl:17][CH2:13][C@H:11]1[O:12][C@H:6]2[C@H:7]([N:8]=[C:4]([NH:3][CH2:1][CH3:2])[S:5]2)[C@@H:9]([OH:16])[C@@H:10]1[OH:15]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 24808478Thiamet G, >=98% (HPLC)

Product 1

HCID 71511789CID 71511789Yield 16.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

In a 5 mL seal vial equipped with a stir bar was added (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (30.00 mg; 0.12 mmol; 1.00 eq.) and 1-chloropyrrolidine-2,5-dione (24.20 mg; 0.18 mmol; 1.50 eq.) in N,N-dimethylformamide (1.00 ml) followed by triphenylphosphine (63.38 mg; 0.24 mmol; 2.00 eq.). After the clear solution was stirred at 50° C. for 2 h, color became wine red. The reaction was stirred for overnight before it is concentrated and dissolved in 2 mL MeOH. Yamazen HPLC Channel1 (acidic condition, 220 nm, 55 g Interchim column, product efflux at H2O/ACN=75/25) was used to isolate 5.4 mg (12%) of the title compound as a white solid once lyophilized.

Workup

  1. customIn a 5 mL seal vial
  2. customequipped with a stir bar
  3. stirringThe reaction was stirred for overnight before it
  4. concentrationis concentrated
  5. dissolutiondissolved in 2 mL MeOH

Sources & evidence

ORD record
ord-aec6e42d8bf044f09f084f496db05d78
Source dataset
uspto-grants-2014_11
Patent number
US08884023B2

Reaction notes

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