Ethyl isocyanatoacetate → Tris(hydroxymethyl)aminomethane

HRID 489251Notes

Reaction equation

HRID 489251 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@:12]3([C@H:18]([C:19]4[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=4)[CH2:17][NH:16][CH2:15]3)[N:11]([CH3:27])[C:10]2=[O:28])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[N:29]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:30]=[O:31].C1[CH2:42][O:41]CC1.C[N:44]([CH:46]=[O:47])C>>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][NH:29][C:30]([N:16]1[CH2:17][C@@H:18]([C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)[C@:12]2([N:11]([CH3:27])[C:10](=[O:28])[N:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)[C:13]2=[O:14])[CH2:15]1)=[O:31])[CH3:37].[CH2:42]([OH:41])[C:32]([NH2:29])([CH2:33][OH:35])[CH2:46][OH:47].[N-:44]=[C:46]=[O:47]

Participants

6

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 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 105034IsocyanateHCID 60054734HCID 60054734, compound

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-d50d3603938444529e9116c1eb1dfb11
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Reaction notes

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