Hydrochloric Acid → HCID 89619582, compound

HRID 1775844Notes

Reaction equation

HRID 1775844 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH2:4][C:5]([O:7][CH3:8])=[O:6].[C:17]([C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl>CN(C=O)C.C(Cl)Cl>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([NH:2][C@@H:3]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)[CH2:4][C:5]([O:7][CH3:8])=[O:6])=[O:26])=[CH:28][CH:29]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 74034-tert-Butylbenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89675761HCID 89675761, compound

Product 1

HCID 89619582HCID 89619582, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Prepared using General Procedure 7. A solution of (S)-methyl 3-amino-4-(4-hydroxyphenyl)butanoate hydrochloride (2.1 g, 8.7 mmol), 4-(tert-butyl)benzoic acid (1.6 g, 9.0 mmol) and DIEA (3.5 ml, 18.8 mmol) in DMF (20 mL) and DCM (20 mL) was treated with HATU (3.3 g, 8.5 mmol). After 1 h, the mixture was poured onto 1M HCl (100 mL) and extracted with EA (3×50 mL). The combined organic extracts were washed successively with 1M HCl (50 mL), water (50 mL) and brine (20 mL), then dried over MgSO4 and concentrated. The resulting residue was purified by chromatography (EA/hexane) to provide 2.3 g (72%) of (S)-methyl 3-(4-(tert-butyl)benzamido)-4-(4-hydroxyphenyl)butanoate as white needles. LCMS-ESI (m/z) calculated for C22H27NO: 369.4. found 370.0 [M+H]+, tR=2.52 min (Method 6).

Workup

  1. customPrepared
  2. extractionextracted with EA (3×50 mL)
  3. washThe combined organic extracts were washed successively with 1M HCl (50 mL), water (50 mL) and brine (20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by chromatography (EA/hexane)

Sources & evidence

ORD record
ord-aa3a2fa60d154135969c7cdf45fbde06
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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