Ammonia → HCID 131710550, compound

HRID 1731228Notes

Reaction equation

HRID 1731228 reaction equation
[NH2:1][C@H:2]([C:24]([NH:26][C@H:27]([C:35]([NH:37][C@H:38]([C:46]([NH:48][C@H:49]([C:56]([NH:58][C@H:59]([C:64]([NH:66][C@H:67]([C:89]([NH:91][C@H:92]([C:99]([NH:101][C@H:102]([C:107]([OH:109])=[O:108])[CH2:103][CH:104]([CH3:106])[CH3:105])=[O:100])[CH2:93][O:94][C:95]([CH3:98])([CH3:97])[CH3:96])=[O:90])[CH2:68][S:69]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:65])[C@H:60]([CH2:62][CH3:63])[CH3:61])=[O:57])[CH2:50][O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:47])[C@@H:39]([CH3:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:36])[CH2:28][S:29][CH2:30][NH:31][C:32]([CH3:34])=[O:33])=[O:25])[CH2:3][S:4]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.II.O=C1O[C@H]([C@H](CO)O)C(O)=C1O.N>C(O)C(F)(F)F.O.C([O-])(=O)C.[NH4+].C(Cl)Cl>[NH2:1][C@H:2]([C:24]([NH:26][C@H:27]([C:35]([NH:37][C@H:38]([C:46]([NH:48][C@H:49]([C:56]([NH:58][C@H:59]([C:64]([NH:66][C@H:67]([C:89]([NH:91][C@H:92]([C:99]([NH:101][C@H:102]([C:107]([OH:109])=[O:108])[CH2:103][CH:104]([CH3:106])[CH3:105])=[O:100])[CH2:93][O:94][C:95]([CH3:98])([CH3:97])[CH3:96])=[O:90])[CH2:68][SH:69])=[O:65])[C@H:60]([CH2:62][CH3:63])[CH3:61])=[O:57])[CH2:50][O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:47])[C@@H:39]([CH3:45])[O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:36])[CH2:28][S:29][CH2:30][NH:31][C:32]([CH3:34])=[O:33])=[O:25])[CH2:3][SH:4]

Participants

9

Reactant 4

HCID 222AmmoniaHCID 807IodineHCID 54670067L-Ascorbic AcidHCID 131710551HCID 131710551, compound

Product 1

HCID 131710550HCID 131710550, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 64092,2,2-TrifluoroethanolSolvent2×HCID 517165Ammonium AcetateSolvent

Procedure

0.47 g of H-Cys(Trt)-Cys(Acm)-Thr(But)-Ser(But)-Ile-Cys(Trt)-Ser(But)-Leu-OH in 15 ml of trifluoroethanol are added over the course of 10 minutes to a vigorously stirred mixture of 18 ml of methylene chloride, saturated with iodine, and 180 ml of trifluoroethanol. 2 minutes after completion of the addition, a solution of 3.2 g of ascorbic acid in 60 ml of water and 30 ml of 1 M ammonium acetate are added, the solution is brought to pH 5.6 with dilute ammonia and the trifluoroethanol is very largely removed under reduced pressure. The mixture is then taken up in 100 ml of chloroform-methanol (95:5) and the organic phase is twice washed with water. After drying over sodium sulphate, the mixture is evaporated and the product shown in the title is purified by gel filtration on Sephadex-LH 20 (column: 2 × 100 cm). Eluant: chloroform-methanol (1:1).

Workup

  1. addition2 minutes after completion of the addition
  2. customthe trifluoroethanol is very largely removed under reduced pressure
  3. washthe organic phase is twice washed with water
  4. dry with materialAfter drying over sodium sulphate
  5. customthe mixture is evaporated
  6. filtrationis purified by gel filtration on Sephadex-LH 20 (column: 2 × 100 cm)

Sources & evidence

ORD record
ord-3082b5cb212f4b779a6edb9495a716d7
Source dataset
uspto-grants-1976_11
Patent number
US03994871

Reaction notes

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