Tris(hydroxymethyl)aminomethane → HCID 69536270, compound

HRID 1017986Notes

Reaction equation

[C:1]([NH:9][C@@H:10]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:43])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])=[O:32])=[C:26]([O:41][CH3:42])[CH:25]=2)=[CH:17][CH:16]=1)[CH2:11][C:12]([OH:14])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)[C:45](N)(CO)[CH2:46][OH:47].[O:52]1CCC[CH2:53]1>O>[N:30]([CH2:27][CH2:26][OH:41])([CH2:31][CH2:53][OH:52])[CH2:45][CH2:46][OH:47].[C:1]([NH:9][C@@H:10]([C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:43])[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])=[O:32])=[C:26]([O:41][CH3:42])[CH:25]=2)=[CH:19][CH:20]=1)[CH2:11][C:12]([OH:14])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (R)-3-benzoylamino-3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetyl-amino}phenyl)-propanoic acid [1.0 g, Example 5(a)], tris(hydroxymethyl)aminomethane (0.208 g), tetrahydrofuran (80 ml) and water (15 ml) was stirred at 50° C. for 1.5 hours, then cooled to room temperature and then evaporated. The residue was recrystallised from ethanol to give the title compound as a white crystalline solid (1.1 g), m.p 135-140° C. (with decomposition). [Elemental analysis:—C, 61.6; H, 6.1; N, 9.5%. Calculated for C33H32N4O6.C4H11NO3.H2O:—C, 61.75; H, 6.3; N, 9.7%].

Workup

temperaturecooled to room temperature
customevaporated
customThe residue was recrystallised from ethanol

Sources & evidence

ORD record: ord-d07ba901c36a4310838055860748cb03
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479519B1

Reaction notes

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