4-Chlorobenzoic Acid → HCID 68770829, compound

HRID 1175115Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.Cl.[NH2:12][C:13]([CH3:40])([CH3:39])[C:14]([NH:16][C@H:17]([B:26]1[O:30][C@@H:29]2[CH2:31][C@@H:32]3[CH2:35][C@H:34]([C@:28]2([CH3:38])[O:27]1)[C:33]3([CH3:37])[CH3:36])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1)=[O:15].C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:12][C:13]([CH3:40])([CH3:39])[C:14]([NH:16][C@H:17]([B:26]2[O:30][C@@H:29]3[CH2:31][C@@H:32]4[CH2:35][C@H:34]([C@:28]3([CH3:38])[O:27]2)[C:33]4([CH3:37])[CH3:36])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=2)=[O:15])=[O:8])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 22 °C

Procedure

To a solution of 4-chlorobenzoic acid (0.087 g, 0.553 mmol) in CH2Cl2 were added 2-amino-2-methyl-N-{(1R)-2-(3-methylphenyl)-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}propanamide hydrochloride (0.20 g, 0.503 mmol), HOBt (0.075 g, 0.553 mmol), 4-methylmorpholine (0.204 g, 2.42 mmol) and EDCI (0.106 g, 0.553 mmol). The reaction mixture was allowed to stir at 22° C. After 12 h, the reaction mixture was quenched with a saturated solution of sodium bicarbonate and the product partitioned into DCM. The organic layer was dried over MgSO4, filtered and concentrated to give the title compound (0.210 g, 77%). LC/MS: Rt=2.29 min, ES+537 (Formic Acid method).

Workup

customthe reaction mixture was quenched with a saturated solution of sodium bicarbonate
customthe product partitioned into DCM
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-812ab179905b48e1bf9ea790029b9fee
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838673B2

Reaction notes

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