Tris(hydroxymethyl)aminomethane → HCID 10178574, compound

HRID 2306873Notes

Reaction equation

HRID 2306873 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]([CH2:13][S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[NH2:17])[C:6]2[O:7][CH2:8][O:9][CH2:10][C:5]=2[CH:4]=1.[CH3:22][C:23]([CH3:28])([CH3:27])[C:24](Cl)=[O:25].C(O)C(N)(CO)CO>ClCCl.C(N(C(C)C)CC)(C)C.CN(C1C=CN=CC=1)C>[Cl:2][C:3]1[CH:12]=[C:11]([CH2:13][S:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[NH:17][C:24](=[O:25])[C:23]([CH3:28])([CH3:27])[CH3:22])[C:6]2[O:7][CH2:8][O:9][CH2:10][C:5]=2[CH:4]=1

Participants

7

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 62493Pivaloyl chlorideHCID 22629953HCID 22629953, compound

Product 1

HCID 10178574HCID 10178574, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

The product from step 1 (75 mg, 0.22 mmol) was dissolved in a mixture of dichloromethane and diisopropyl ethyl amine (4 mL , ˜40:1), PS DMAP resin (0.10 g, Argonaut 1.41 mmol/g) was added in followed by 2,2-dimethylpropanoyl chloride (0.15 mL, 1.25 mmol). The reaction was agitated for 24 hours and then treated with PS trisamine (Argonaut 4.27 mmol/g) for 6 h filtered and the solvent removed under a stream of nitrogen. The residue was chromatographed on silica to give the title product 55 mg (65%). 1H NMR (CDCl3) δ 9.87 (s, 1 H), 8.45 (dd, 1 H), 7.39 (dd, 1 H), 7.33 (dt, 1 H), 7.00 (dt, 1 H), 6.80 (dd, 2 H), 4.98 (s, 2 H), 4.77 (s, 2 H), 3.84 (s, 2 H), 1.28 (s, 9 H); MS (ESI+) for C20H22ClNO3S m/z 392 (M+H)+.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. customthe solvent removed under a stream of nitrogen
  4. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-1a68259417e342fa917dacfe2113bf43
Source dataset
uspto-grants-2004_12
Patent number
US06828446B2

Reaction notes

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