MTBE acetone water → HCID 178487476, compound

HRID 734928Notes

Reaction equation

HRID 734928 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][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C@H:24]([CH3:41])[C:25]([O:27][CH:28](OC(ON1C(=O)CCC1=O)=O)[CH3:29])=[O:26])[CH:18]=[CH:17]2.CC([O:46][CH3:47])(C)C.CC(C)=[O:50].O>>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C@H:24]([CH3:41])[C:25]([O:27][CH2:28][CH2:29][O:50][C:47]([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:46])=[O:26])[CH:18]=[CH:17]2

Participants

4

Reactant 3

HCID 86610273MTBE acetone waterHCID 866102811-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]ethyl (2S)-2-[6-methoxy(2-naphthyl)]propanoateHCID 178511262HCID 178511262, compound

Product 1

HCID 178487476HCID 178487476, compoundYield 9%

Procedure

Following the general nucleophilic carbamoylation procedure, tranexamic acid (6.9 g, 43.9 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]ethyl (2S)-2-[6-methoxy(2-naphthyl)]propanoate (ca. 6.2 g, 14.9 mmol) were reacted in the MTBE/acetone/water mixture (160 mL) to yield the title compound 27 (579 mg, 9% yield) as a colorless powder after work-up, purification by silica gel column chromatography using ethyl acetate/hexane mixtures from 2:1 to 4:1 as eluent, and subsequent mass-guided preparative HPLC. 1H NMR (400 MHz, DMSO-d6): δ=0.76-0.94 (m, 2H), 1.10-1.92 (m, 13H), 1.98-2.14 (m, 1H), 2.66-2.86 (m, 2H), 3.82-3.95 (m, 4H), 6.64-6.76 (m, 1H), 7.10-7.17 (m, 1H), 7.24-7.50 (m, 3H), 7.63-7.80 (m, 3H), 11.99 (br.s, 1H). MS (ESI) m/z 480.16 (M+Na)+; 456.18 (M−H)−.

Sources & evidence

ORD record
ord-8abb5af6be9b4aa89aadd20d46574a5b
Source dataset
uspto-grants-2009_09
Patent number
US07592369B2

Reaction notes

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