Tetrahydrofuran → HCID 68431243, compound

HRID 2246246Notes

Reaction equation

[C:1]([C:5]([NH:7][C@@H:8]([C@@H:13]([C:15]1[O:19][N:18]=[C:17]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][C:21]=2[Cl:30])[N:16]=1)[CH3:14])[C:9]([O:11]C)=[O:10])=[O:6])([CH3:4])([CH3:3])[CH3:2].O1CCCC1.O.[OH-].[Li+]>O>[C:1]([C:5]([NH:7][C@@H:8]([C@@H:13]([C:15]1[O:19][N:18]=[C:17]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][C:21]=2[Cl:30])[N:16]=1)[CH3:14])[C:9]([OH:11])=[O:10])=[O:6])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of the ester from Step C (1 g, 2.11 mmol) in 50 mL of a 4:1 solution of tetrahydrofuran:water at 0° C. was added a solution of lithium hydroxide monohydrate (0.3 g, 6.33 mmol) in 8 mL of water. After stirring at 0° C. for 1 h, the THF was removed by evaporation under reduced pressure and 10 mL of 2N hydrochloric acid was added. The aqueous solution was extracted with three portions of ethyl acetate. The combined organic layers were washed with saturated aqueous brine, dried over sodium sulfate and concentrated in vacuo to afford the product which was used in the next step without purification. LC/MS 360.0 (M+1-BOC).

Workup

customthe THF was removed by evaporation under reduced pressure and 10 mL of 2N hydrochloric acid
additionwas added
extractionThe aqueous solution was extracted with three portions of ethyl acetate
washThe combined organic layers were washed with saturated aqueous brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customto afford the product which
customwas used in the next step without purification

Sources & evidence

ORD record: ord-e901019675324371862a4d184b90c95f
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687492B2

Reaction notes

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