Hydrochloric Acid → N-[(Benzyloxy)carbonyl]-L-tyrosyl-D-alanylglycine

HRID 1249299Notes

Reaction equation

HRID 1249299 reaction equation
[NH:1]([C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([O:22]C)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>CO.O>[NH:1]([C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13769326HCID 13769326, compound

Product 1

HCID 12802573N-[(Benzyloxy)carbonyl]-L-tyrosyl-D-alanylglycine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of Z-Tyr-D-Ala-Gly-OMe (27) (4.57 g, 0.01 mol) in MeOH (10 ml) was added 1 N NaOH (20 ml, 0.02 mol) at 0° with stirring. The suspension was stirred for 2 hr at 0° C., diluted with water (80 ml), and neutralized with 1 N HCl (20 ml). The precipitated crystals were collected by suction, washed with water and dried under reduced pressure to give Z-Tyr-D-Ala-Gly.OH (28) (3.59 g, 81.0%), mp 102°-104° C. (AcOEt) (lit.* mp 124° C.); [α]D22 18.0° (C=1.0, DMF), (lit.* [α]D22 16.7° (c=0.54, DMF)); NMR (DMSO-d6)δ: 1.16 (3H, d, J=7 Hz, CH3), 2.60-2.90 (2H, m, CH2), 3.80 (2H, d, J=6 Hx, CH2PhOH), 4.10-4.45 (2H, m, 2CH), 5.02 (2H, s, CH2O), 6.63-7.20 (4H, m, HOPh-), 7.40 (5H, s, ArH), 8.10-8.30 (2H, br, 2 NH), 9.10-9.40 (1H, br, OH). Rf (IV)=0.20.

Workup

  1. stirringThe suspension was stirred for 2 hr at 0° C.
  2. customThe precipitated crystals were collected by suction
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-f66a560c6e3541e397275dd39b18c4c8
Source dataset
uspto-grants-1986_12
Patent number
US04629784

Reaction notes

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