p-Toluenesulfonic acid → 3-Hydroxy-2-methyl-2-(methylamino)propanoic acid tert-butyl ester

HRID 1669926Notes

Reaction equation

HRID 1669926 reaction equation
[C:1]([O:5][C:6](=[O:20])[C:7]([NH:11][CH2:12]C(OC(C)(C)C)=O)([CH3:10])[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC(=O)C(NC(C1C=CC(OC)=CC=1)C1C=CC(OC)=CC=1)(C)CO)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>>[C:1]([O:5][C:6](=[O:20])[C:7]([CH3:10])([NH:11][CH3:12])[CH2:8][OH:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 11825571HCID 11825571, compoundHCID 866345862-[N-(tert-butoxycarbonyl)methylamino]-3-hydroxy-2-methylpropanoic acid tert-butyl ester

Product 1

HCID 108562593-Hydroxy-2-methyl-2-(methylamino)propanoic acid tert-butyl esterYield 69.1%

Procedure

A 255 mg portion of alcohol 11 (0.88 mmol) was treated with 1 eq p-toluenesulfonic acid (167 mg) as described in the preparation of 12a. The resulting solid was added to 15 mL of 10% Na2CO3 and extracted with 3×15 mL of EtOAc. The combined organic layers were subject to the usual work up. Purification via silica gel column chromatography (10% CH3OH in CH2Cl2) afforded 12b (115 mg, 69%) as a colorless oil: 1H NMR (CDCl3) δ 1.24 (3H, s), 1.48 (9H, s), 2.32 (3H, s), 3.52 (1H, d, J=10.8), 3.64 (1H, d, J=10.8). HRMS Calcd for C9H19NO3: 189.13649. Found 189.13627. Anal. (C9H19NO3) Calcd C, 57.12; H, 10.12, N, 7.40. Found C, 55.87; H, 10.05, N, 7.18.

Workup

  1. extractionextracted with 3×15 mL of EtOAc
  2. customPurification via silica gel column chromatography (10% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-0a7bf4c04ea645de8d97149c0e2cb99e
Source dataset
uspto-grants-2011_08
Patent number
US07989649B2

Reaction notes

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