Sodium Bicarbonate → HCID 58981690, compound

HRID 1182281Notes

Reaction equation

HRID 1182281 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:14])[C@@H:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:5].NC[C@@H](O)[C@@H](NC(=O)OC(C)(C)C)C.C(=O)(O)[O-].[Na+].[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[S:40](Cl)(=[O:42])=[O:41]>ClCCl.O>[OH:14][C@@H:3]([CH2:2][NH:1][S:40]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][N:34]=1)(=[O:42])=[O:41])[C@@H:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH3:5]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 58981716HCID 58981716, compoundHCID 58981761HCID 58981761, compound

Product 1

HCID 58981690HCID 58981690, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3.06 g (15.0 mmol) of tert-butyl (1S,2S)-3-amino-2-hydroxy-1-methylpropylcarbamate & tert-butyl (1S,2R)-3-amino-2-hydroxy-1-methylpropylcarbamate in 100 mL of dichloromethane was added 3.78 g (45.0 mmol) of sodium bicarbonate and 50 mL of water. The reaction mixture was cooled to 0° C. and 16.5 mL (16.5 mmol) of a 1.0 M solution of 2-pyridinesulfonyl chloride in dichloromethane was added gradually over 20 min. The reaction mixture was stirred at room temperature for 16 h. The layers were then separated and the organic layer was dried over anhydrous magnesium sulfate, and concentrated under vacuum to afford the crude product. This product was purified via silica gel chromatography eluting with ethyl acetate:hexane (8:2) to afford 2.0 g (34%) of tert-butyl (1S,2S)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate & tert-butyl (1S,2R)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate as a pale yellow oil. 1H-NMR (300 MHz, CDCl3): δ 8.72 (m, 1H), 8.07–7.92 (m, 2H), 7.51 (m, 1H), 6.25, 6.08 (2br s, 1H), 4.83-4.64 (m, 2H), 3.74–3.47 (m, 3H), 3.27–3.19 (m, 1H), 1.23, 1.22 (2s, 9H), 1.12 (m, 3H).

Workup

  1. customThe layers were then separated
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customto afford the crude product
  5. customThis product was purified via silica gel chromatography
  6. washeluting with ethyl acetate:hexane (8:2)

Sources & evidence

ORD record
ord-01d575cf249c4f7796ac94b2c7415385
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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