Formaldehyde → HCID 89668532, compound

HRID 1482387Notes

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:23][C:24]3[N:25]=[CH:26][S:27][CH:28]=3)[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:29]=O>C1(C)C=CC=CC=1.C(OCC)C.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[O:21]=[C:20]1[O:22][CH2:29][N:18]([C:16]([O:15][CH2:14][CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[O:17])[C@H:19]1[CH2:23][C:24]1[N:25]=[CH:26][S:27][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(thiazol-4-yl)propanoic acid (Fmoc-Ala(4-Thz)-OH, Compound SP818) (50 g, 127 mmol), camphorsulfonic acid (2.10 g, 9.04 mmol) and paraformaldehyde (110 g, 3.66 mol) were dissolved in toluene (2 l) under a nitrogen atmosphere, and the mixture was stirred at 80° C. for two days. The reaction solution was diluted with diethyl ether and sequentially washed with an aqueous sodium bicarbonate solution and brine. The resulting organic extract was dried over sodium sulfate and then concentrated under reduced pressure to afford (S)-(9H-fluoren-9-yl)methyl 5-oxo-4-(thiazol-4-ylmethyl)oxazolidine-3-carboxylate (Compound SP817) (40.0 g, 98%) as a crude product.

Workup

washsequentially washed with an aqueous sodium bicarbonate solution and brine
extractionThe resulting organic extract
dry with materialwas dried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-02d0fc38da964c2fbbceb1c6782dcbae
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409952B2

Reaction notes

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