Sulfuric Acid → N-(Triphenylmethyl)-L-asparagine

HRID 618434Notes

Reaction equation

HRID 618434 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[C:10](O)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.OS(O)(=O)=O.C(OC(=O)C)(=O)C.[OH-].[Na+]>C(O)(=O)C.O>[CH:26]1[CH:27]=[CH:28][C:23]([C:10]([NH:5][C:4]([CH2:3][C@H:2]([NH2:1])[C:7]([OH:9])=[O:8])=[O:6])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6267(-)-AsparagineHCID 6457TriphenylcarbinolHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide

Product 1

HCID 7408309N-(Triphenylmethyl)-L-asparagine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Bpoc-Asn(Trt)--OH: H-Asn(Trt)--OH was prepared according to the procedure of Sieber and Riniker (40) with the following modifications. H-Asn-OH (13.2 g, 0.1 mol), trityl alcohol (52 g, 0.2 mol), conc. H2SO4 (6.1 mL, 0.115 mol) were suspended in glacial acetic acid (300 mL) for 10 min. Acetic anhydride (9 mL, 0.2 mol) was added and the reaction was heated to 60° C. After 4 h the solution was slowly added to cold water (600 mL) and adjusted to pH 6 by addition of 10 N NaOH. After 1 h at 0° C., white crystals were collected and washed thoroughly with water and toluene. Drying under vacuum for 24 h yielded white crystals (36 g, 94%). mp>240 dec., lit. >240 dec.

Workup

  1. customwhite crystals were collected
  2. washwashed thoroughly with water and toluene
  3. customDrying under vacuum for 24 h

Sources & evidence

ORD record
ord-7c06b6ebc76f468689461bd9ee367f15
Source dataset
uspto-grants-1999_09
Patent number
US05952497

Reaction notes

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