Acetic Anhydride → HCID 178475069, compound

HRID 2167014Notes

Reaction equation

HRID 2167014 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][CH2:8][NH:9][C:10]([NH:12][S:13]([C:16]1[C:17]([CH3:29])=[C:18]([CH3:28])[C:19]2[O:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]=2[C:26]=1[CH3:27])(=[O:15])=[O:14])=[NH:11])[C:3]([OH:5])=[O:4].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[C:30]([NH:1][C@@H:2]([CH2:6][CH2:7][CH2:8][NH:9][C:10]([NH:12][S:13]([C:16]1[C:17]([CH3:29])=[C:18]([CH3:28])[C:19]2[O:23][C:22]([CH3:25])([CH3:24])[CH2:21][C:20]=2[C:26]=1[CH3:27])(=[O:15])=[O:14])=[NH:11])[C:3]([OH:5])=[O:4])(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178427586HCID 178427586, compound

Product 1

HCID 178475069HCID 178475069, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(S)-2-Amino-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl) guanidino)pentanoic acid (H-L-Arg(Pbf)-OH) (1.0 eq.) is dissolved in pyridine (0.25 M) and acetic anhydride (1.2 eq.) is added to acylate the primary amine, after 1 h the reaction is quenched with aqueous acid, extracted with ethyl acetate, and purified by chromatography to afford (S)-2-acetamido-5-(3-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl) guanidino)pentanoic acid (Ac-L-Arg(Pbf)-OH).

Workup

  1. customafter 1 h the reaction is quenched with aqueous acid
  2. extractionextracted with ethyl acetate
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-49cac3d09a504c3dbe96f9ebd63c1781
Source dataset
uspto-grants-2015_06
Patent number
US09044464B2

Reaction notes

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