Ethyl isocyanatoacetate → Tris(hydroxymethyl)aminomethane

HRID 1792883Notes

Reaction equation

HRID 1792883 reaction equation
ClC1C=C([N:9]2[C:13](=[O:14])[C@@]3([C@H](C4C=CC(C#N)=CC=4)CNC3)N(C)[C:10]2=[O:28])C=C(Cl)C=1.[N:29]([CH2:32][C:33]([O:35]CC)=O)=C=O.C1C[O:41][CH2:40]C1.CN(C=O)C>>[CH2:40]([OH:41])[C:32]([NH2:29])([CH2:33][OH:35])[CH2:13][OH:14].[N-:9]=[C:10]=[O:28]

Participants

5

Reactant 3

HCID 76283Ethyl isocyanatoacetateHCID 119947544-[(5S,9R)-3-(3,5-Dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-9-yl]-benzonitrileHCID 21974620tetrahydrofuran N,N-dimethylformamide

Product 2

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 105034Isocyanate

Procedure

To a solution of Example 15 (24.9 mg, 0.06 mmol) in 1 ml THF/DMF (9/1), was added ethyl isocyanatoacetate (11.6 mg, 0.089 mmol), and the reaction mixture was stirred overnight at RT. The titled compound was obtained (33.3 mg) after treatment with PS-Trisamine (Argonaut, 73 mg, 0.267 mmol) and PS-Isocyanate (Argonaut, 85 mg, 0.122 mmol). Retention time: 1.99 min., 544 (M+1); (LCMS conditions: LC Micromass platform (APCI+, DAD (210–400 nm)), Column: TSK gel Super ODS 4.6 mm ID×5 cm, Flow rate: 2.75 mL/min, Gradient: from 100% eluent A to 100% eluent B in 2 min., with a plateau with 100% eluent B during 1 min. Eluent A: H2O (0.05% TFA), Eluent B: CH3CN/H2O/TFA (80/20/0.05)).

Sources & evidence

ORD record
ord-851aa17fb191445b8977f327b3ffde44
Source dataset
uspto-grants-2006_07
Patent number
US07078420B2

Reaction notes

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