MTBE acetone water → HCID 178454741, compound

HRID 386973Notes

Reaction equation

[CH2:1]1[CH2:6][C@H:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3][C@H:2]1[CH2:10][NH2:11].[CH3:12][CH:13]([CH3:35])[C:14]([O:16][CH2:17][C:18]1(OC(ON2C(=O)CCC2=O)=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:15].CC([O:40][CH3:41])(C)C.CC(C)=[O:44].O>>[CH3:35][CH:13]([CH3:12])[C:14]([O:16][CH:17]([CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[O:44][C:41]([NH:11][CH2:10][C@H:2]1[CH2:3][CH2:4][C@H:5]([C:7]([OH:9])=[O:8])[CH2:6][CH2:1]1)=[O:40])=[O:15]

Participants

Reactant 3

HCID 86610273MTBE acetone water

HCID 86610296HCID 86610296, compound

HCID 178511262HCID 178511262, compound

Product 1

HCID 178454741HCID 178454741, compoundYield 43%

Procedure

Following the general nucleophilic carbamoylation procedure, tranexamic acid (472 mg, 3.0 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]cyclohexylmethyl 2-methylpropanoate (683 mg, 2.0 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 51 (327 mg, 43% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.81-0.94 (br. m, 2H), 1.00-1.36 (br. m, 14H), 1.58-1.74 (br. m, 8H), 1.83-1.91 (br. m, 2H), 2.09 (tt, J=12.0, 3.6 Hz, 1H), 2.51 (hept., J=6.8 Hz, 1H), 2.74-2.86 (m, 2H), 6.41 (d, J=5.2 Hz, 1H), 7.40 (br. t, J=5.6 Hz, 1H), 11.97 (br. s, 1H). MS (ESI) m/z 406.18 (M+Na)+; 382.19 (M−H)−.

Sources & evidence

ORD record: ord-430ca065d41840cc9f87b1173a89514b
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372881B2

Reaction notes

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