Acetic Acid → HCID 131712095, compound

HRID 126788Notes

Reaction equation

HRID 126788 reaction equation
[NH:1]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H](C([NH:29][C@H:30]([C:35](OC)=[O:36])[CH2:31][CH2:32][S:33][CH3:34])=O)CC1C=CC=CC=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.[Li+].[BH4-].[C:48]([OH:51])(=[O:50])[CH3:49].CO>O1CCCC1.CCOC(C)=O.CCCCCC>[NH:1]([C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][C@H:49]([C:48]([OH:51])=[O:50])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1.[NH2:29][C@H:30]([CH2:35][OH:36])[CH2:31][CH2:32][S:33][CH3:34]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 4148881Lithium borohydrideHCID 12888623HCID 12888623, compound

Product 1

HCID 131712095HCID 131712095, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of Boc-Tyr-DAla-Phe-Met-OCH3 (5.8 g) (prepared in Step C of Example 1A) in 100 ml of dry tetrahydrofuran under nitrogen was added 1.0 g of LiBH4. After stirring at room temperature for 1 hour, 6 ml of acetic acid was added slowly followed by 50 ml of methanol to destroy excess LiBH4. Evaporation of the solution gave an oil which was dissolved in 250 ml of EtOAc and washed with 1 N HCl (4×25 ml), 1 N NaHCO3 (3×50 ml) and saturated NaCl (3×50 ml). Evaporation of the MgSO4 dried EtOAc solution gave a foam which was dissolved in 25 ml of hot EtOAc and diluted with 100 ml of hexane to give a solid. The solid was recrystallized from 50 ml of isopropanol and 100 ml of water to give 5.7 g (93%) of Boc-Tyr-DAla-Phe-Methioninol, m.p. 107-100° C., [α]D25 =0.08° (c, 1.00 in methanol).

Workup

  1. customto destroy excess LiBH4
  2. customEvaporation of the solution
  3. customgave an oil which
  4. washwashed with 1 N HCl (4×25 ml), 1 N NaHCO3 (3×50 ml) and saturated NaCl (3×50 ml)
  5. customEvaporation of the MgSO4 dried EtOAc solution
  6. customgave a foam which
  7. customto give a solid
  8. customThe solid was recrystallized from 50 ml of isopropanol and 100 ml of water

Sources & evidence

ORD record
ord-5c38526c2ac14d7fa205c6d823bfaef4
Source dataset
uspto-grants-1981_03
Patent number
US04254024

Reaction notes

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