HCID 131712095, compound → HCID 131712096, compound

HRID 126789Notes

Reaction equation

HRID 126789 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[NH2:37][C@H:38]([CH2:43][OH:44])[CH2:39][CH2:40][S:41][CH3:42]>C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[NH2:37][C@H:38]([CH2:43][OH:44])[CH2:39][CH2:40][S:41][CH3:42].[CH3:19][C:27]([OH:29])=[O:28]

Participants

4

Reactant 1

HCID 131712095HCID 131712095, compound

Product 1

HCID 131712096HCID 131712096, compoundYield 159.9%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of 2.47 g of Boc-Tyr-DAla-Phe-Methioninol in 20 ml of 10% anisole in TFA was stirred for 30 min and then evaporated to a syrup. The syrup was dissolved in 20 ml of methanol, water, acetic acid (50:49:1) and applied to an Amberlite XAD-2 column (44-74 μm, 2.7×60 cm). Elution of the sample at 5 ml/min with a linear gradient formed from 2 liters each of water:methanol:acetic acid (94:5:1) to methanol:water:acetic acid (94:5:1) gave a product peak which was evaporated to a syrup. The syrup was dissolved in 20 ml of isopropanol and diluted with 150 ml of ether to give 1.85 g (82%) of H-Tyr-DAla-Phe-Methioninol HOAc, m.p. 110°-120° C., [α]D25 =24.05° (C, 0.98, methanol).

Workup

  1. customevaporated to a syrup
  2. dissolutionThe syrup was dissolved in 20 ml of methanol
  3. washElution of the sample at 5 ml/min with a linear gradient
  4. customformed from 2 liters each of water:methanol:acetic acid (94:5:1) to methanol:water:acetic acid (94:5:1)
  5. customgave a product peak which
  6. customwas evaporated to a syrup
  7. dissolutionThe syrup was dissolved in 20 ml of isopropanol
  8. additiondiluted with 150 ml of ether

Sources & evidence

ORD record
ord-2f23cbcaa4de4bf79b53439234c16f6a
Source dataset
uspto-grants-1981_03
Patent number
US04254024

Reaction notes

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