Hexane → HCID 57202916, compound

HRID 36528Notes

Reaction equation

C([S:4][CH2:5][C@H:6]([C:19]([F:22])([F:21])[F:20])[C:7]([NH:9][C@@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C:12]([OH:14])=[O:13])=[O:8])(=O)C.[OH-].[NH4+].C(OCC)(=O)C.CCCCCC>O.CO.C(O)(=O)C>[F:20][C:19]([F:21])([F:22])[C@@H:6]([CH2:5][SH:4])[C:7]([NH:9][C@@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C:12]([OH:14])=[O:13])=[O:8]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of the (S,S) isomer product of Example 36 (0.91 g., 2.7 mmol.) in water maintained at 0° C. under argon was treated with ammonium hydroxide (5M solution, 10 mL, 50 mmol.) and stirred for 5 minutes. The reaction was quenched at 0° C. with 140 mL of 10% potassium bisulfate and then extracted with ethyl acetate (4×). The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo to yield 1.0 g. of a yellow solid. The crude reaction product was triturated with hexane:ethyl acetate to yield 0.78 g. of the title (S,S) isomer product as an off white solid; m.p. 155°-156° C., TLC Rf =0.18 (ethyl acetate:hexane:acetic acid, 100:100:1). [α]D =+26.1° (c=0.81, methanol).

Workup

additionA suspension of the (S,S)
customThe reaction was quenched at 0° C. with 140 mL of 10% potassium bisulfate
extractionextracted with ethyl acetate (4×)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto yield 1.0 g
customThe crude reaction product
customwas triturated with hexane
customethyl acetate to yield 0.78 g

Sources & evidence

ORD record: ord-4895039cbdc54a41ac38d87e689f0a60
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05414017

Reaction notes

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