MTBE acetone water → HCID 178454742, compound

HRID 734950Notes

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].[C:12]([O:17][CH2:18][C:19]1(OC(ON2C(=O)CCC2=O)=O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)(=[O:16])[CH2:13][CH2:14][CH3:15].CC([O:40][CH3:41])(C)C.CC(C)=[O:44].O>>[C:12]([O:17][CH:18]([CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]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:16])[CH2:13][CH2:14][CH3:15]

Participants

Reactant 3

HCID 86610273MTBE acetone water

HCID 86610295HCID 86610295, compound

HCID 178511262HCID 178511262, compound

Product 1

HCID 178454742HCID 178454742, compoundYield 43%

Procedure

Following the general nucleophilic carbamoylation procedure, tranexamic acid (472 mg, 3.0 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]cyclohexylmethyl butanoate (683 mg, 2.0 mmol) were reacted in the MTBE/acetone/water mixture (16 mL) to yield the title compound 50 (329 mg, 43% yield) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (400 MHz, DMSO-d6): δ=0.83-0.95 (br. m, 5H), 0.96-1.37 (br. m, 8H), 1.47-1.57 (m, 2H), 1.58-1.74 (br. m, 8H), 1.83-1.92 (br. m, 2H), 2.09 (tt, J=12.0, 3.6 Hz, 1H), 2.26 (td, J=7.6, 0.8 Hz, 2H), 2.74-2.86 (m, 2H), 6.44 (d, J=5.6 Hz, 1H), 7.39 (t, J=6.0 Hz, 1H), 11.97 (br. s, 1H). MS (ESI) m/z 406.24 (M+Na)+; 382.23 (M−H)−.

Sources & evidence

ORD record: ord-019cc3301d3c457fbd2bae5ea3d83a77
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592369B2

Reaction notes

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