Formic Acid → HCID 131733611, compound

HRID 1751164Notes

Reaction equation

HRID 1751164 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([N:15]1[CH2:47][CH2:46][CH2:45][C@H:16]1[C:17]([NH:19][C@H:20]([C:42]([NH2:44])=[O:43])[CH2:21][S:22][C:23]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:18])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C(O)=O.C(OCC)(=O)C>O>[NH2:1][C@H:2]([C:13]([N:15]1[CH2:47][CH2:46][CH2:45][C@H:16]1[C:17]([NH:19][C@H:20]([C:42]([NH2:44])=[O:43])[CH2:21][S:22][C:23]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:18])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 8857Ethyl AcetateHCID 131733610HCID 131733610, compound

Product 1

HCID 131733611HCID 131733611, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the Boc-Trp-Pro-Cys(Trt)-NH2 (100 gm), added formic acid (800 ml) at temperature of about 20° C. to about 35° C. Stirred for 60 minutes at same temperature and charged ethyl acetate, DM water to the reaction mass and separated the aqueous and organic layers. Washed the organic layer with DM water and separated the layers. Taken organic layer and cooled to about 0° C. to about 10° C. and adjusted pH to 10-12 with 8N aqueous sodium hydroxide solution. Heated the solution to about 25° C. to about 35° C. and separated the organic layer. Concentrated the organic layer under reduced pressure to obtain the residue, which was crystallized from isopropyl ether to obtain H-Trp-Pro-Cys(Trt)-NH2 as white solid material.

Workup

  1. customseparated the aqueous and organic layers
  2. washWashed the organic layer with DM water
  3. customseparated the layers
  4. temperatureTaken organic layer and cooled to about 0° C. to about 10° C.
  5. temperatureHeated the solution to about 25° C. to about 35° C.
  6. customseparated the organic layer
  7. concentrationConcentrated the organic layer under reduced pressure
  8. customto obtain the residue, which
  9. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-9c86284293a14989bdedd382061a07b1
Source dataset
uspto-grants-2015_10
Patent number
US09156885B2

Reaction notes

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