Triethylamine → HCID 86653290, compound

HRID 1805225Notes

Reaction equation

HRID 1805225 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]=[C:32]=[O:34])=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 66705807HCID 66705807, compound

Product 1

HCID 86653290HCID 86653290, compoundYield 253.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred suspension of (S)-4-[2-(4-amino-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (600 mg, example 14 (b)) in dichloromethane (10 ml) were added sequentially triethylamine (0.52 ml) and triphosgene (206 mg) and the mixture was heated at 50° C. for 18 h. The mixture was then concentrated in vacuo and to the residue was added diethyl ether. After stirring for 10 min at room temperature the resulting crystals were removed by filtration. The filtrate was concentrated in vacuo to give (S)-4-[2-(4-isocyanato-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (610 mg, 94%) as a yellow oil which was used immediately in the next step without further purification.

Workup

  1. concentrationThe mixture was then concentrated in vacuo and to the residue
  2. additionwas added diethyl ether
  3. customwere removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a9f1e855f8ef403fb9c1239763a2931c
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Reaction notes

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