Sulfuric Acid → HCID 67462821, compound

HRID 915750Notes

Reaction equation

[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([C:29]([OH:31])=[O:30])[CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(OC[CH2:37][CH2:38][CH3:39])(=O)C.S(=O)(=O)(O)O.Cl[CH2:46]Cl>>[C:38]([O:30][C:29](=[O:31])[C@@H:19]([CH2:20][O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[NH:18][C:16]([O:15][CH2:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:17])([CH3:37])([CH3:39])[CH3:46]

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 6344Dichloromethane

HCID 31272Butyl Acetate

HCID 7019719Fmoc-D-Ser(Bzl)-OH

Product 1

HCID 67462821HCID 67462821, compoundYield 77%

Procedure

N-[(9H-Fluoren-9-yl)methoxycarbonyl]-O-(benzyl)-D-serine (0.710 g, 1.70 mmole) in dichloromethane (8 mL) was treated with 1-butyl acetate (3 mL) and concentrated sulfuric acid (40 μL) in a sealed flask at 0° C. Upon completion (TLC), the reaction was quenched with of dichloromethane (10 mL) and saturated aqueous potassium bicarbonate (15 mL). The organic layer was washed with distilled water, and evaporated. The resulting residue was purified by flash column chromatography (98:2 dichloromethane/methanol) to yield the title compound as a colorless oil (0.292 g, 77%);

Workup

customUpon completion (TLC), the reaction was quenched with of dichloromethane (10 mL) and saturated aqueous potassium bicarbonate (15 mL)
washThe organic layer was washed with distilled water
customevaporated
customThe resulting residue was purified by flash column chromatography (98:2 dichloromethane/methanol)

Sources & evidence

ORD record: ord-ae480f33f6ff4297aab2e326c73e53a7
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268125B2

Reaction notes

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