Water → HCID 11416557, compound

HRID 1482390Notes

Reaction equation

HRID 1482390 reaction equation
[C:1](Cl)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[CH3:19][NH:20][C@H:21]([C:24]([OH:26])=[O:25])[CH2:22][OH:23].C(=O)([O-])[O-].[Na+].[Na+].O>O1CCCC1.CCCCCC.C(OCC)C>[CH:16]1[C:17]2[CH:5]([CH2:4][O:3][C:1]([N:20]([CH3:19])[C@@H:21]([CH2:22][OH:23])[C:24]([OH:26])=[O:25])=[O:2])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 7009640Methylserine

Product 1

HCID 11416557HCID 11416557, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of FmocCl (1.35 g, 5.21 mmol) in tetrahydrofuran (5 mL) was added to a solution of N-methyl-L-serine (Compound SP822) (621 mg, 5.21 mmol) and sodium carbonate (580 mg, 5.47 mmol) in tetrahydrofuran (15 mL)-water (20 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 20 minutes, followed by addition of diethyl ether (10 mL) and hexane (5 mL). The resulting mixture was extracted with water, and the aqueous layer was washed with ether (15 mL), followed by addition of concentrated hydrochloric acid (1 mL). The resulting mixture was extracted with ethyl acetate three times, and the organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The resulting crude product was purified by reverse-phase silica gel column chromatography (0.05% aqueous trifluoroacetic acid solution/0.05% trifluoroacetic acid-acetonitrile solution) to afford (Compound SP823) (1.49 g, 84%).

Workup

  1. extractionThe resulting mixture was extracted with water
  2. washthe aqueous layer was washed with ether (15 mL)
  3. additionfollowed by addition of concentrated hydrochloric acid (1 mL)
  4. extractionThe resulting mixture was extracted with ethyl acetate three times
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude product was purified by reverse-phase silica gel column chromatography (0.05% aqueous trifluoroacetic acid solution/0.05% trifluoroacetic acid-acetonitrile solution)
  8. customto afford (Compound SP823) (1.49 g, 84%)

Sources & evidence

ORD record
ord-28f160afb2d8480881a35be2297cab18
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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