Triethylamine → HCID 131711190, compound

HRID 2419486Notes

Reaction equation

HRID 2419486 reaction equation
[NH2:1][C@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:23]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:24]([C:28](ON1C(=O)CCC1=O)=[O:29])[CH:25]([CH3:27])[CH3:26].CCN(CC)CC>CN(C=O)C>[NH:23]([C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[C@H:24]([C:28]([NH:1][C@H:2]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:29])[CH:25]([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 98768Boc-Val-osuHCID 7408727O-(Phenylmethyl)-L-threonine phenylmethyl ester

Product 1

HCID 131711190HCID 131711190, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

H-Thr(Bzl)-OBzl hemioxalate (58 g, 168.4 mmol) was suspended in DMF (700 ml) and stirred with Boc-Val-OSu (48 g, 153.1 mmol) and Et3N (16 ml) at 0° C for 1 hr, 4° C for 72 hrs and 25° C for 24 hrs. It was necessary during this time to add at intervals additional Et3N in order to maintain the pH between 7 and 8. The reaction mixture was worked up as in Example 2 to yield an oil which crystallized from EtOAc with petroleum ether, yield 40.8 g (53.5%); mp 99°-100.5° C; [α]D25 -26.0° (c 1, MeOH). Anal. Calcd for C28H38N2O6 (498.62): C, 67.45; H, 7.68; N, 5.62. Found: C, 67.57; H, 7.55; N, 5.70.

Workup

  1. temperatureto maintain the pH between 7 and 8
  2. customto yield an oil which
  3. customcrystallized from EtOAc with petroleum ether, yield 40.8 g (53.5%)

Sources & evidence

ORD record
ord-bcafc9a29a5c45d895a404c42b9a752a
Source dataset
uspto-grants-1978_08
Patent number
US04105652

Reaction notes

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