Phosphoric Acid → HCID 23458724, compound

HRID 1680015Notes

Reaction equation

HRID 1680015 reaction equation
Cl.Cl.[NH2:3][CH:4]([CH:8]1[NH:12][CH:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C:10]2([CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:24][CH2:23]2)[S:9]1)[C:5]([OH:7])=[O:6].[C:34](Cl)([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N(CC)CC)C.P(=O)(O)(O)O>ClCCl>[CH2:16]([O:15][C:13]([CH:11]1[C:10]2([CH2:23][CH2:24][N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:26][CH2:27]2)[S:9][CH:8]([CH:4]([NH:3][C:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:5]([OH:7])=[O:6])[NH:12]1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 70574841HCID 70574841, compound

Product 1

HCID 23458724HCID 23458724, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

9.1 g (0.0177 mole) of alpha-amino-4-benzyloxycarbonyl-8-phenyl-1-thia-3,8-diazaspiro[4.5]decane-2-acetic acid dihydrochloride (obtained in 5.3) are suspended in 150 ml of dichloromethane. After cooling to -20° C., 18,6 g (0.0668 mole) of trityl chloride are added all at once. While maintaining the temperature at about -20° C., the suspension is slowly treated over the course of 1 hour with 17.6 g (0.17 mole) of triethylamine in 100 ml of dichloromethane. The reaction mixture is stirred for 1 hour at a temperature of from -10 to -20° C. and then left to stand overnight in a refrigerator, whereafter it is poured onto an ice-water mixture (pH about 11) and neutralized to about pH 6 by the addition of 85% phosphoric acid. The aqueous phase is extracted three times with 100 ml of dichloromethane. The combined extracts are washed with water and dried over anhydrous sodium sulfate, followed by evaporation to dryness under high vacuum on a waterbath at a temperature of from 20° to 25° C. The 4-benzyloxycarbonyl-8-phenyl-alpha-tritylamino-1-thia-3,8-diazaspiro[4.5]-decane-2-acetic acid thus obtained is used, without further purification, in step 7.3.

Workup

  1. temperatureWhile maintaining the temperature at about -20° C.
  2. waitleft
  3. waitto stand overnight in a refrigerator, whereafter it
  4. extractionThe aqueous phase is extracted three times with 100 ml of dichloromethane
  5. washThe combined extracts are washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customfollowed by evaporation to dryness under high vacuum on a waterbath at a temperature of from 20° to 25° C

Sources & evidence

ORD record
ord-14c814a31ab34488aa6363d413158fe8
Source dataset
uspto-grants-1981_06
Patent number
US04271172

Reaction notes

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