Ammonia → HCID 178425968, compound

HRID 623274Notes

Reaction equation

HRID 623274 reaction equation
[NH:1]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:2]([C:22](O)=[O:23])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:21])[NH:8][S:9]([C:12]1[C:19]([CH3:20])=[CH:18][C:16]([CH3:17])=[CH:15][C:13]=1[CH3:14])(=[O:11])=[O:10].C[N:33]1CCOCC1.N>C1COCC1>[NH:1]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[C@H:2]([C:22]([NH2:33])=[O:23])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:21])[NH:8][S:9]([C:12]1[C:13]([CH3:14])=[CH:15][C:16]([CH3:17])=[CH:18][C:19]=1[CH3:20])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 178425970HCID 178425970, compound

Product 1

HCID 178425968HCID 178425968, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Boc-Arg(Mts)-OH prepared from 1.3 kg of Boc-Arg(Mts)-OH·CHA are dissolved at ambient temperature in 6.2 kg of THF, and 280 g of NMM are added. To this solution 380 g of SBCF are added at -10° C., and stirring is continued at -10° C. for 15 minutes, and then 0.69 kg of 29% aqueous ammonia are added at -10° C. The medium is stirred at -10° C. for 30 mins. and then at 5° C., and the development of the reaction is followed by HPLC. The reaction is terminated after 30 mins. The medium is poured into 31.5 kg of water, and then 19.2 kg of AcOEt are added. After stirring for 15 mins, the organic phase is washed by:

Workup

  1. stirringThe medium is stirred at -10° C. for 30 mins
  2. customat 5° C.
  3. customThe reaction is terminated after 30 mins
  4. additionThe medium is poured into 31.5 kg of water
  5. addition19.2 kg of AcOEt are added
  6. stirringAfter stirring for 15 mins
  7. washthe organic phase is washed by:

Sources & evidence

ORD record
ord-c95d04b4db994a56a0c0cfa0a9307477
Source dataset
uspto-grants-1988_09
Patent number
US04774319

Reaction notes

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