Acetic Anhydride → HCID 54275696, compound

HRID 2089103Notes

Reaction equation

[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[CH2:12][CH3:13])[CH2:8][CH:7]([NH:14][CH2:15][C@@H:16]([C:18]1[CH:19]=CC(O)=[C:22]([NH:24][CH:25]=O)[CH:23]=1)[OH:17])[CH2:6]2)[CH3:2].[BH4-].[Na+].C(O[C:34](=O)[CH3:35])(=O)C.O1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>>[CH2:1]([N:14]([CH:7]1[CH2:8][C:9]2[C:5](=[CH:4][C:3]([CH2:1][CH3:2])=[C:11]([CH2:12][CH3:13])[CH:10]=2)[CH2:6]1)[CH2:15][C@@H:16]([C:18]1[CH:19]=[CH:42][C:41]([O:40][CH2:39][C:38]2[CH:35]=[CH:34][CH:8]=[CH:7][CH:6]=2)=[C:22]([NH:24][CH3:25])[CH:23]=1)[OH:17])[C:3]1[CH:4]=[CH:5][CH:9]=[CH:10][CH:11]=1

Participants

Reactant 4

HCID 7918Acetic Anhydride

HCID 312751,4-Dioxane

HCID 4311764Sodium borohydride

HCID 54072328HCID 54072328, compound

Product 1

HCID 54275696HCID 54275696, compound

Conditions

Temperature: 90 °C

Procedure

The product of Example 22 (260 mg) is dissolved in dioxan (20 mL). Sodium borohydride (90 mg) is added followed by the dropwise addition of acetic anhydride (142 mg). The reaction mixture is stirred at 90° C. The reaction is shown to be complete by TLC after 4 hours. The solvent is removed in vacuo and the residue is partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. The product is purified by flash column chromatography (silica, n-hexane/ethyl acetate 4:1). TLC (silica, n-hexane/ethyl acetate 2:1 Rf=0.65).

Workup

customThe solvent is removed in vacuo
customthe residue is partitioned between ethyl acetate (100 mL) and water (100 mL)
dry with materialThe organic layer is dried over MgSO4
filtrationfiltered
customthe solvent is removed in vacuo
customThe product is purified by flash column chromatography (silica, n-hexane/ethyl acetate 4:1)

Sources & evidence

ORD record: ord-bdf0674302a74a468d4ccaf439504bc1
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436017B2

Reaction notes

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