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Chlorotrimethylsilane → N-(Triphenylmethyl)-D-serine

HRID 420107
Notes
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Reaction equation

HRID 420107 reaction equation
[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C[Si](Cl)(C)C.C[Si](C)(C)N[Si](C)(C)C.[C:22](Cl)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl.CO.C(N(CC)CC)C>[C:22]([NH:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 6456Trityl chlorideHCID 13838HexamethyldisilazaneHCID 71077D-Serine

Product 1

HCID 12042811N-(Triphenylmethyl)-D-serine

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×
HCID 6344DichloromethaneSolvent2×
HCID 8471TriethylamineSolvent

Conditions

Temperature
37.5 °C

Procedure

To dichloromethane (400 ml), D-serine (50 g) was added at ambient temperature under nitrogen atmosphere to form a suspension and then trimethylsilyl chloride (61.92 g) and hexamethyldisilazane (107.5 ml) was added to the suspension in 10-15 minutes at ambient temperature. The reaction mixture was refluxed at 35-40° C. for 3 hours and then it was cooled to 0° C. To this mixture, a solution of anhydrous methanol (22.83 g) in dichloromethane (50 ml) was added at 0° C. and the mixture was allowed to reach at room temperature. Triethylamine (48.14 g) was slowly added to it at 25-30° C. and then trityl chloride (132.63 g) was added in 3 lots to the mixture at an interval of 10 minutes. The reaction mixture was then stirred for overnight under nitrogen at ambient temperature. After completion of the reaction, methanol (76.12 g) was added at ambient temperature in 10-15 minutes and the solvent was recovered under vacuum at 40-45° C. Hexane (400 ml) and 5% citric acid solution (750 ml) was added to the recovered solid and filtered. The solid product obtained was washed with water (750 ml) and hexanes (200 ml) and then filtered. The filtered solid was washed with hexanes (200 ml) and dried to obtain the titled product. Yield=125 gm.

Workup

  1. customto form a suspension
  2. temperatureit was cooled to 0° C
  3. customto reach at room temperature
  4. additionwas added at ambient temperature in 10-15 minutes
  5. customthe solvent was recovered under vacuum at 40-45° C
  6. additionHexane (400 ml) and 5% citric acid solution (750 ml) was added to the recovered solid
  7. filtrationfiltered
  8. customThe solid product obtained
  9. washwas washed with water (750 ml) and hexanes (200 ml)
  10. filtrationfiltered
  11. washThe filtered solid was washed with hexanes (200 ml)
  12. customdried

Sources & evidence

ORD record
ord-26a814a9578f47638aa23fc211318b5f
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08093426B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes