Hydrochloric Acid → HCID 19805555, compound

HRID 2248137Notes

Reaction equation

HRID 2248137 reaction equation
N[CH:2]([CH2:6][CH2:7][CH3:8])[C:3]([OH:5])=[O:4].C([N:11]([CH2:14][CH3:15])CC)C.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.Cl.[OH-].[Na+]>CO.C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:11][CH2:14][CH2:15][C:17]2[CH:22]=[CH:21][C:20]([CH2:8][CH2:7][CH2:6][CH2:2][C:3]([OH:5])=[O:4])=[CH:19][CH:18]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 824DL-norvalineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 14798Sodium Hydroxide

Product 1

HCID 19805555HCID 19805555, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 6.0 g. (21 mMol) of the aminopentanoic acid from c) and 5.3 g. (52.5 mMol) triethylamine in 100 ml. methylene chloride are added portionwise at 0° C. 4.4 g. (21 mMol) 4-chlorobenzenesulphonic acid chloride, followed by stirring for 1 hour at 0° C. and for 1 hour at ambient temperature. The reaction mixture is shaken out with 2N hydrochloric acid and the organic phase is dried over anhydrous sodium sulphate and evaporated. There are obtained 9.8 g. of the ester in the form of a pale yellow oil which is converted into the free acid by heating with 30 ml. 2N aqueous sodium hydroxide solution in 30 ml. methanol to 50° C. and subsequent acidification with concentrated hydrochloric acid. The yield is 7.4 g. (85% of theory) of colourless crystals; m.p. 118°-120° C.

Workup

  1. additionTo a suspension of 6.0 g
  2. dry with materialthe organic phase is dried over anhydrous sodium sulphate
  3. customevaporated
  4. customThere are obtained 9.8 g
  5. temperatureby heating with 30 ml
  6. customto 50° C.

Sources & evidence

ORD record
ord-11a08be708ff40e1bd094132d20914ff
Source dataset
uspto-grants-1991_08
Patent number
US05037990

Reaction notes

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