Hydrochloric Acid → 2-amino-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}acetamide

HRID 1676099Notes

Reaction equation

HRID 1676099 reaction equation
[CH3:1][CH:2]([CH3:30])[CH2:3][C@H:4]([NH:18][C:19](=[O:29])[CH2:20][NH:21]C(=O)OC(C)(C)C)[B:5]1[O:9][C@@H:8]2[CH2:10][C@@H:11]3[CH2:14][C@H:13]([C@:7]2([CH3:17])[O:6]1)[C:12]3([CH3:16])[CH3:15].Cl>C(Cl)Cl.O1CCOCC1>[NH2:21][CH2:20][C:19]([NH:18][C@H:4]([B:5]1[O:9][C@@H:8]2[CH2:10][C@@H:11]3[CH2:14][C@H:13]([C@:7]2([CH3:17])[O:6]1)[C:12]3([CH3:15])[CH3:16])[CH2:3][CH:2]([CH3:30])[CH3:1])=[O:29]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53362904tert-butyl [2-({(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]carbamate

Product 1

HCID 533629602-amino-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl [2-({(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]carbamate (2.5 g, 5.9 mmol) in DCM (15 mL) was added 4M HCl in dioxane (5.9 mL). The reaction mixture was allowed to stir for 2 h and concentrated to give 2-amino-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}acetamide which was used in the next step without purification.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-246ac1a3ac424ccd8511bc57e33b3304
Source dataset
uspto-grants-2011_08
Patent number
US08003819B2

Reaction notes

Loading…