Hydrochloric Acid → HCID 22816341, compound

HRID 1680576Notes

Reaction equation

HRID 1680576 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([NH:20][C@H:21]([C:26]([NH:28][CH2:29][C:30]([NH:32][C@H:33]([C:41]([CH:43]1[C:50]2([NH2:52])[CH2:51][CH:46]3[CH2:47][CH:48]([CH2:53][C:44]1([C:54]([O:56]C)=[O:55])[CH2:45]3)[CH2:49]2)=[O:42])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:31])=[O:27])[CH2:22][CH2:23][S:24][CH3:25])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.[OH-].[K+].Cl>CO>[C:1]([NH:8][C@H:9]([C:18]([NH:20][C@@H:21]([C:26]([NH:28][CH2:29][C:30]([NH:32][C@H:33]([C:41]([CH:43]1[C:50]2([NH2:52])[CH2:51][CH:46]3[CH2:47][CH:48]([CH2:53][C:44]1([C:54]([OH:56])=[O:55])[CH2:45]3)[CH2:49]2)=[O:42])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:31])=[O:27])[CH2:22][CH2:23][S:24][CH3:25])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 70566959HCID 70566959, compound

Product 1

HCID 22816341HCID 22816341, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.1 g of methyl Boc-L-tyrosylmethionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylate in 10 ml of methanol is added 10 ml of water. The pH is adjusted to 13.0 with a 4 M solution of potassium hydroxide and held at pH 13-13.5 for 2.5 hours. The pH is adjusted to 11.0 with 12 N hydrochloric acid, and the methanol is removed under vacuum. The residual aqueous solution is adjusted to pH 2.0 by the slow addition of hydrochloric acid causing the product to crystallize. The product is collected by filtration and washed with water then dried for two hours at 50° C. and 0.1 mm of pressure. The residue is dissolved in a 6 N solution of ammonia. The excess ammonia is removed under vacuum and the remaining aqueous solution is adjusted to pH 4.0 with 1 N acetic acid. The product crystallizes and is collected by filtration, washed with water and dried for 16 hours at 50° C. and 0.1 mm pressure to give Boc-L-tyrosyl-D-methionyl-glycyl-L-phenylalanyl-3-amino-1-adamantanecarboxylic acid which is represented by the following formula ##STR26##

Workup

  1. customthe methanol is removed under vacuum
  2. additionThe residual aqueous solution is adjusted to pH 2.0 by the slow addition of hydrochloric acid causing the product
  3. customto crystallize
  4. filtrationThe product is collected by filtration
  5. washwashed with water
  6. customthen dried for two hours at 50° C.
  7. dissolutionThe residue is dissolved in a 6 N solution of ammonia
  8. customThe excess ammonia is removed under vacuum
  9. customThe product crystallizes
  10. filtrationis collected by filtration
  11. washwashed with water
  12. customdried for 16 hours at 50° C.

Sources & evidence

ORD record
ord-f2faf31abd5446ad87a1440d04f60553
Source dataset
uspto-grants-1981_06
Patent number
US04273704

Reaction notes

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