Sodium Hydroxide → HCID 136359930, compound

HRID 1969679Notes

Reaction equation

[C:1](=[O:42])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][C@H:3]1[CH2:7][C@H:6]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][N:17](S(C5C=CC(C)=CC=5)(=O)=O)[C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[C@H:5]([CH2:30][CH3:31])[CH2:4]1.[CH:43]1([NH2:46])[CH2:45][CH2:44]1.[OH-].[Na+]>O1CCOCC1>[CH:43]1([NH:46][C:1](=[O:42])[O:2][C@H:3]2[CH2:7][C@H:6]([C:8]3[N:12]4[C:13]5[CH:19]=[CH:18][NH:17][C:14]=5[N:15]=[CH:16][C:11]4=[N:10][N:9]=3)[C@H:5]([CH2:30][CH3:31])[CH2:4]2)[CH2:45][CH2:44]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a scalemic mixture enriched in (1R,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl 4-nitrophenyl carbonate (Example #41 Step O, 0.211 g, 0.357 mmol) in 1,4-dioxane (1.5 mL) was added cyclopropylamine (0.102 g, 1.79 mmol). After about 1 h, 1N aqueous sodium hydroxide (1.5 mL, 1.5 mmol) was added and the reaction mixture was heated at about 60° C. for about 30 min then cooled to ambient temperature. The layers were separated and the aqueous layer was extracted with DCM (3×5 mL). The combined organic layers were concd under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-10% MeOH in EtOAc to give (1R,3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl cyclopropylcarbamate (0.085 g, 67%): LC/MS (Table 1, Method b) Rt=1.73 min; MS m/z: 355 (M+H)+.

Workup

temperaturethen cooled to ambient temperature
customThe layers were separated
extractionthe aqueous layer was extracted with DCM (3×5 mL)
customThe residue was purified by silica gel chromatography
washeluting with 0-10% MeOH in EtOAc

Sources & evidence

ORD record: ord-6e342af63d3345f5be8685b0411d88cb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426411B2

Reaction notes

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