Diisopropylethylamine → HCID 67041964, compound

HRID 62775Notes

Reaction equation

[F:1][C:2]1[C:10]([O:11][CH:12]([CH3:14])[CH3:13])=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:15][CH:16]([CH3:18])[CH3:17].CC[N:21]([CH:25]([CH3:27])[CH3:26])C(C)C.[CH2:28](P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.ClC1C(OC(CC)CC)=[CH:54][C:50]([C:51]([OH:53])=[O:52])=[CH:49]C=1OCC>CCOC(C)=O>[F:1][C:2]1[C:3]([O:15][CH:16]([CH3:18])[CH3:17])=[CH:4][C:5]([C:6]([NH:21][C:25]2[CH:26]=[CH:54][C:50]([C:51]([O:53][CH3:28])=[O:52])=[CH:49][CH:27]=2)=[O:8])=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 4-fluoro-3,5-diisopropoxybenzoic acid (8) (54 mg, 0.21 mmol), DIPEA (110 μL, 0.632 mmol) and T3P (50% solution in EtOAc) (310 μL, 0.527 mmol) in EtOAc (1 mL) was stirred at RT for 10 min before a solution of methyl 4-aminobenzoate (9) (35 mg, 0.23 mmol) in EtOAc (1 mL) was added dropwise and the mixture was stirred at 40° C. for 20 h. The reaction mixture was adsorbed on to silica and purified by silica gel chromatography (4 g, 0-100% EtOAc in isohexane), then (4 g, 0-10% MeOH in DCM) to afford methyl 4-(4-fluoro-3,5-diisopropoxybenzamido)benzoate (10) (32 mg, 51% purity). The material was taken on in the subsequent reaction step without further purification.

Workup

additionwas added dropwise
custompurified by silica gel chromatography (4 g, 0-100% EtOAc in isohexane)

Sources & evidence

ORD record: ord-b2a3ee37cce441ca87fb02d73b402285
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447028B2

Reaction notes

Loading…