Dichloromethane → HCID 22884085, compound

HRID 1598440Notes

Reaction equation

C(OC([NH:8][C@@H:9]([CH2:27][S:28]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:26])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=2[CH3:25])[CH2:13][CH2:12]1)=O)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(Cl)[Cl:63]>>[ClH:63].[ClH:63].[NH2:8][C@@H:9]([CH2:27][SH:28])[CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:26])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=2[CH3:25])[CH2:13][CH2:12]1

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 22884115HCID 22884115, compound

Product 1

HCID 22884085HCID 22884085, compound

Conditions

Temperature: 20 °C

Procedure

The product from step D and triethylsilane (0.54 mL, 3.4 mmol) were dissolved in methylene chloride (6 mL). To this solution was added trifluoroacetic acid (3 mL) and the reaction stirred at 20° C. for 30 min. The reaction was evaporated to dryness and partitioned between hexane and water. The aqueous phase was injected onto a 40×100 mm Waters PrepPak® reverse phase HPLC column (Delta-Pak™ C18 15 μm, 100 Å), and pure product isolated by gradient elution using 100% Solvent A (0.1% trifluoroacetic acid in water) to 50% Solvent A/50% Solvent B (0.1% trifluoroacetic acid in acetonitrile) over 50 min at a flow rate of 40 mL/min. Combined fractions were evaporated, dissolved in water and passed through a Biorad AG® 3×4 ion exchange resin column (100-200 mesh, Cl-form). The column eluant was lyophilized to give the title compound as a white powder.

Workup

customThe reaction was evaporated to dryness
custompartitioned between hexane and water
customisolated by gradient elution
customover 50 min
customCombined fractions were evaporated
dissolutiondissolved in water

Sources & evidence

ORD record: ord-538c16c7d8204569bcb688783bb3f42a
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05736539

Reaction notes

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