Formic Acid → (2R)-2-amino-3-((triphenylmethyl)sulfanyl)propanamide

HRID 1751160Notes

Reaction equation

HRID 1751160 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:24]([NH2:26])=[O:25])[CH2:3][S:4][C:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)=O.C(Cl)Cl.[OH-].[Na+]>O>[NH2:1][C@H:2]([C:24]([NH2:26])=[O:25])[CH2:3][S:4][C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 284Formic Acid2×HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 57188993HCID 57188993, compound

Product 1

HCID 44432703(2R)-2-amino-3-((triphenylmethyl)sulfanyl)propanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the Boc-Cys(Trt)-NH2 (100 gm), added formic acid (600 ml) at temperature of about 10° C. to about 20° C. Heated the solution to about 20° C. to about 35° C. and stirred for 30 minutes at the same temperature. Added an additional quantity of formic acid (200 ml) and stirred for two hours. Cooled the reaction mass to about 0° C. to about −10° C. and charged methylene chloride (1000 ml), DM water (100 ml) and adjusted pH to 7.5-9.0 with 8N aqueous Sodium hydroxide solution. Heated the solution to about 25° C. to about 35° C. and separated the organic layer and extracted the aqueous layer with methylene chloride (250 ml) and separated the aqueous and organic layer. Combined the organic layer and washed with DM water and concentrated the organic layer under reduced pressure to obtain the residue. The residue was crystallized from hexane (100 ml) to obtain the H-Cys(Trt)-NH2 as white solid material.

Workup

  1. temperatureHeated the solution to about 20° C. to about 35° C.
  2. stirringstirred for two hours
  3. temperatureCooled the reaction mass to about 0° C. to about −10° C.
  4. temperatureHeated the solution to about 25° C. to about 35° C.
  5. customseparated the organic layer
  6. extractionextracted the aqueous layer with methylene chloride (250 ml)
  7. customseparated the aqueous and organic layer
  8. washwashed with DM water
  9. concentrationconcentrated the organic layer under reduced pressure
  10. customto obtain the residue
  11. customThe residue was crystallized from hexane (100 ml)

Sources & evidence

ORD record
ord-7f019f15543c41c4955920f83f941b67
Source dataset
uspto-grants-2015_10
Patent number
US09156885B2

Reaction notes

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