Sulfuric Acid → HCID 70567425, compound

HRID 1660111Notes

Reaction equation

HRID 1660111 reaction equation
C(N(CC)CC)C.ClC(OCC)=O.[C:14]([NH:24][CH2:25][C:26]([OH:28])=O)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].[NH2:29][C@H:30]([C@H:33]([C@@H:35]([C@@H:37]([CH2:39][OH:40])[OH:38])[OH:36])[OH:34])[CH2:31][OH:32].S(=O)(=O)(O)O>C1C=CC=CC=1.CC(C)=O.O.O1CCOCC1.O1CCCC1>[C:14]([NH:24][CH2:25][C:26]([NH:29][C@H:30]([C@H:33]([C@@H:35]([C@@H:37]([CH2:39][OH:40])[OH:38])[OH:36])[OH:34])[CH2:31][OH:32])=[O:28])([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15]

Participants

10

Reactant 5

HCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14349BenzyloxycarbonylglycineHCID 1890222-Amino-2-deoxyhexitol

Product 1

HCID 70567425HCID 70567425, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolventHCID 22015841Benzene methyl ketoneSolvent

Procedure

A mixture of 275 ml. of dry tetrahydrofuran and 275 ml. of dry dioxane was cooled to -5° and 12.88 ml. (9.35 g., 0.092 mole) of triethylamine, 8.74 ml. (9.96 g., 0.092 mole) of ethyl chloroformate and 19.23 g. (0.092 mole) of N-carbobenzyloxyglycine were added. The mixture was stirred for 15 min. at -5° and then a cold (0°-5°) solution of 16.65 g. (0.092 mole) of 2-amino-2-deoxy-D-glucitol in 40 ml. of water was added in one portion. The cooling bath was removed and the mixture was allowed to stir at ambient temperature for four hours. The solvent was evaporated in vacuum at 30°-40° and the residue was stirred overnight with 500 ml. of ethanol. Filtration furnished 30 g. of a solid. The solid was recrystallized from 700 ml. of methanol to give 21 g. of product. Tlc shows the product to be pure (silica gel plate--benzene/methyl ketone/88% formic acid 60:25:25--methanolic sulfuric acid development).

Workup

  1. additionA mixture of 275 ml
  2. customa cold (0°-5°) solution of 16.65 g
  3. customThe cooling bath was removed
  4. stirringto stir at ambient temperature for four hours
  5. customThe solvent was evaporated in vacuum at 30°-40°
  6. stirringthe residue was stirred overnight with 500 ml
  7. filtrationFiltration
  8. customfurnished 30 g
  9. customThe solid was recrystallized from 700 ml
  10. customof methanol to give 21 g

Sources & evidence

ORD record
ord-4e75e23cfe214b278b145b1725430a1f
Source dataset
uspto-grants-1981_12
Patent number
US04307072

Reaction notes

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