Tris(hydroxymethyl)aminomethane → HCID 69591907, compound

HRID 1827583Notes

Reaction equation

HRID 1827583 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][C:13]1[CH:14]=[C:15]([CH:41]=[CH:42][CH:43]=1)[CH2:16][N:17]([S:29]([C:32]1[C:37]([CH3:38])=[CH:36][C:35]([CH3:39])=[CH:34][C:33]=1[CH3:40])(=[O:31])=[O:30])[C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C:26](O)=[O:27])=[CH:20][CH:19]=1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.C(O)C(N)(CO)CO.[N-]=C=O>C(Cl)Cl.C(OCC)(=O)C.CN(C1C=CN=CC=1)C>[CH3:40][C:33]1[CH:34]=[C:35]([CH3:39])[CH:36]=[C:37]([CH3:38])[C:32]=1[S:29]([N:17]([C:18]1[CH:19]=[CH:20][C:21]([CH:24]=[CH:25][C:26](=[O:27])[N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:22][CH:23]=1)[CH2:16][C:15]1[CH:41]=[CH:42][CH:43]=[C:13]([O:12][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:6]2)[CH:14]=1)(=[O:30])=[O:31]

Participants

10

Reactant 6

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 8471TriethylamineHCID 31268PyrrolidineHCID 105034IsocyanateHCID 111923Propylphosphonic anhydrideHCID 69591877HCID 69591877, compound

Product 1

HCID 69591907HCID 69591907, compoundYield 39.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of pyrrolidine (11.7 μl, 0.14 mmol) in 0.3 mL methylene chloride was added to 3-{4-[[3-(tetrahydro-pyran-2-yloxy)-benzyl]-(2,4,6-trimethylbenzenesulfonyl)-amino]-phenyl}-acrylic acid (0.050 g, 0.09 mmol). Triethylamine (0.07 mL, 0.50 mmol), 1-propanephosphonic acid cyclic anhydride (0.056 mL of a 50 wt. % solution in ethyl acetate, 0.190 mmol), and catalytic DMAP were added. The reaction mixture was stirred at room temperature for 48 hr. PS-trisamine resin (0.050 g) and PS-isocyanate (0.050 g) resin was added, and the reaction mixture was stirred at room temperature for two hours. The resin was filtered off and the filtrate was concentrated. The residue was purified by preparative TLC to afford 0.021 g of the title compound of Step A.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for two hours
  2. filtrationThe resin was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-10dda84b9a59486a92c1091f0c82fe29
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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