L-Pyroglutamic Acid → HCID 67366841, compound

HRID 215801Notes

Reaction equation

[C:1]([O:5][C:6](=[O:29])[NH:7][C@@H:8]1[CH2:13][CH2:12][C@@H:11]([C@@H:14]([OH:28])[CH2:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[N:24]=3)[N:19]=[CH:18][CH:17]=2)[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.N1C(=O)CC[C@H]1C(O)=O>CS(C)=O>[C:1]([O:5][C:6](=[O:29])[NH:7][C@@H:8]1[CH2:13][CH2:12][C@@H:11]([C:14](=[O:28])[CH2:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[N:24]=3)[N:19]=[CH:18][CH:17]=2)[O:10][CH2:9]1)([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of {(3R,6S)-6-[(1S)-1-hydroxy-2-(6-methoxy-[1,5]naphthyridin-4-yl)-ethyl]-tetrahydro-pyran-3-yl}-carbamic acid tert-butyl ester (prepared as described in WO 2006/032466, 0.78 g, 1.73 mmol) cooled to −10° C. was added dropwise DIPEA (1.03 mL, 5.90 mmol). A solution of Pyr.SO3 (0.684 g, 48%, 1.1 eq.) in DMSO (2 mL) was added dropwise. The reaction mixture was stirred for 1 h 45 at 0° C. The volatiles were removed under reduced pressure and water (20 mL) was added. The resulting precipitate was filtered and further dried under HV to give a yellow solid (0.518 g, 66% yield).

Workup

customThe volatiles were removed under reduced pressure and water (20 mL)
additionwas added
filtrationThe resulting precipitate was filtered
customfurther dried under HV

Sources & evidence

ORD record: ord-5c680411ad6043e1b07c4c685745a3a8
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193179B2

Reaction notes

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