Water → HCID 68972961, compound

HRID 1272687Notes

Reaction equation

HRID 1272687 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C@H:5]([NH2:13])[CH2:6][C:7]1[S:8][C:9]([Br:12])=[CH:10][CH:11]=1.N[C@H](CC1S[C:23](Br)=[CH:24][CH:25]=1)C(O)=O.[C:27]([O-:30])(O)=[O:28].[Na+].O.[CH2:33](Cl)Cl>>[CH3:2][O:3][C:4](=[O:14])[C@H:5]([NH:13][C:27]([O:30][C:24]([CH3:23])([CH3:25])[CH3:33])=[O:28])[CH2:6][C:7]1[S:8][C:9]([Br:12])=[CH:10][CH:11]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 7016818(R)-2-Amino-3-(5-bromothiophen-2-yl)propanoic acidHCID 68974038(2R)-amino-3-(5-bromo-thiophen-2-yl)-propionic acid methyl ester HCl

Product 1

HCID 68972961HCID 68972961, compound

Procedure

To a suspension of (2R)-amino-3-(5-bromo-thiophen-2-yl)-propionic acid methyl ester HCl (14.0 g, 46.59 mmol) (prepared from commercially available (2R)-amino-3-(5-bromo-thiophen-2-yl)-propionic acid) in DCM (250 mL) was added NaHCO3 (9.78 g, 116.49 mmol), water (100 mL). The solution was stirred for 10 min and Boc-anhydride (12.20 g, 55.91 mmol) was added. The reaction was stirred overnight. The organic layer was separated and washed with brine, dried (Na2SO4) and concentrated under reduced pressure to give 17.0 g of 3-(5-bromo-thiophen-2-yl)-2(R)-tert-butoxycarbonylamino-propionic acid methyl ester.

Workup

  1. stirringThe reaction was stirred overnight
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ce8a7c21637043199a953561f5eefdba
Source dataset
uspto-grants-2007_04
Patent number
US07208601B2

Reaction notes

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